Insecticidal compounds

ABSTRACT

The present invention relates to bis-amide derivatives as defined by the compound of formula (I), to processes and intermediates for preparing them, to methods of using them to control insect, acarine, nematode and mollusc pests, and to insecticidal, acaricidal, nematicidal and molluscicidal compositions comprising them.

RELATED APPLICATION INFORMATION

This application is a 371 of International Application No.PCT/EP2014/078815, filed 19 Dec. 2014, which claims priority to EPPatent Application No. 13199383.4, filed 23 Dec. 2013, the contents ofwhich are incorporated by reference herein.

The present invention relates to bis-amide derivatives, to processes andintermediates for preparing them, to methods of using them to controlinsect, acarine, nematode and mollusc pests, and to insecticidal,acaricidal, nematicidal and molluscicidal compositions comprising them.

Compounds having insecticidal properties are disclosed in EP1714958,JP2006306771, WO2006137376, EP1916236, WO2007017075, WO2008000438,WO2008/074427, WO2009049845 and WO2010127928. There exists a need foralternative methods of control of pests. Preferably, new compounds maypossess improved insecticidal properties, such as improved efficacy,improved selectivity, reduced toxicity, lower tendency to generateresistance or activity against a broader range of pests. Compounds maybe more advantageously formulated or provide more efficient delivery andretention at sites of action, or may be more readily biodegradable.

It has surprisingly been found that certain bisamide derivatives, whichare substituted by a difluoromethoxy bearing arylhaloalkyl group, havebeneficial properties, which makes them particularly suitable for use asinsecticides.

The present invention therefore provides a compound of formula (I)

whereinY is chlorine, bromine, iodine, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄alkoxy or C₁-C₄ haloalkoxy,X₁ is hydrogen, fluorine or methoxyX₂ is hydrogen or cyano, with the condition that if X₂ is cyano, then X₁is hydrogen,R is hydrogen or C₁-C₄ alkylQ is a group selected from Q1, Q2, Q3, Q4 and Q5, whereQ1 is a group of formula (IIa)

Where the substituents W1 are independently selected from, hydrogen,halogen, cyano, nitro, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy orC₁-C₄ haloalkoxy,andn1 is 0, 1 or 2Q2 is a group of formula (IIb)

Where W₂ is selected from, hydrogen, halogen, cyano, C₁-C₄ alkyl, C₁-C₄haloalkyl, C₁-C₄ alkoxy or C₁-C₄ haloalkoxy,Q3 is a group of formula (IIc)

Where W₃ is selected from, hydrogen, halogen, cyano, C₁-C₄ alkyl, C₁-C₄haloalkyl, C₁-C₄ alkoxy or C₁-C₄ haloalkoxy,Q4 is a group of formula (IId)

Where W₄ is selected, hydrogen, halogen, cyano, C₁-C₄ alkyl, C₁-C₄haloalkyl, C₁-C₄ alkoxy or C₁-C₄ haloalkoxy,Q5 is a group of formula (IIe)

Where W₅ is selected from hydrogen, halogen, cyano, C₁-C₄ alkyl, C₁-C₄haloalkyl, C₁-C₄ alkoxy or C₁-C₄ haloalkoxyor an agrochemically acceptable salt thereof.

The compounds of formula (I) may exist in different geometric or opticalisomers (enantiomers and/or diastereoisomers) or tautomeric forms. Thisinvention covers all such isomers and tautomers and mixtures thereof inall proportions as well as isotopic forms such as deuterated compounds.

Each alkyl moiety either alone or as part of a larger group (such asalkoxy, alkoxy-carbonyl, alkylcarbonyl, alkylaminocarbonyl,dialkylaminocarbonyl) is a straight or branched chain and is, forexample, methyl, ethyl, n-propyl, n-butyl, iso-propyl, n-butyl,sec-butyl, iso-butyl or tert-butyl. The alkyl groups are preferably C₁to C₆ alkyl groups, more preferably C₁-C₄ and most preferably C₁-C₃alkyl groups.

Preferably the present invention provides a compound of formula (I)wherein

X₁ is hydrogen, fluorine or methoxy

X₂ is hydrogen or cyano, with the condition that if X₂ is cyano, then X₁is hydrogen, R is hydrogen, methyl or ethyl

Q is a group selected from Q1, Q2, Q3, Q4 and Q5, where

Q1 is a group of formula (IIa)

Where the substituents W₁ is cyano,And n1 is 1Q2 is a group of formula (IIb)

Where W₂ is hydrogen,Q3 is a group of formula (IIc)

Where W₃ is hydrogen,Q4 is a group of formula (IId)

Where W₄ is hydrogenQ5 is a group of formula (IIe)

Where W₅ is hydrogen.

In one preferred embodiment Q1 is a group of formula (IIa)

In one preferred embodiment Q2 is a group of formula (IIb)

In one preferred embodiment Q3 is a group of formula (IIc)

In one preferred embodiment Q4 is a group of formula (IId)

In one preferred embodiment Q5 is a group of formula (IIe)

In one preferred embodiment X₁ is methoxy and X₂ is hydrogen;

In one preferred embodiment X₂ is cyano and X₁ is hydrogen;

A further aspect of the present invention relates to compounds offormula (III)

where Y is chlorine, bromine, iodine, C₁-C₄ alkyl, C₁-C₄ haloalkyl,C₁-C₄ alkoxy or C₁-C₄ haloalkoxy.

Preferably Y is Cl, Br, I, CH₃, CF₃, CHF₂, OCF₃, OCH₃, OCHF₂

The compounds of the structure (III) are useful in the synthesis ofcompounds according to formula (I).

The compounds in Tables A1 to A12 below illustrate the compounds of theinvention.

TABLE A Line n^(o) Y Q 1 Cl 4-Pyridyl 2 Br 4-Pyridyl 3 I 4-Pyridyl 4 CH₃4-Pyridyl 5 Cl 4-Pyridyl-N-oxide 6 Br 4-Pyridyl-N-oxide 7 I4-Pyridyl-N-oxide 8 CH₃ 4-Pyridyl-N-oxide 9 Cl 3-Pyridyl 10 Br 3-Pyridyl11 I 3-Pyridyl 12 CH₃ 3-Pyridyl 13 Cl 3-Pyridyl-N-oxide 14 Br3-Pyridyl-N-oxide 15 I 3-Pyridyl-N-oxide 16 CH₃ 3-Pyridyl-N-oxide 17 Cl4-Cyanophenyl 18 Br 4-Cyanophenyl 19 I 4-Cyanophenyl 20 CH₃4-Cyanophenyl 21 Cl Phenyl 22 Br Phenyl 23 I Phenyl 24 CH₃ Phenyl 25 Cl2-Chlorophenyl 26 Br 2-Chlorophenyl 27 I 2-Chlorophenyl 28 CH₃2-Chlorophenyl 29 Cl 4-Nitrophenyl 30 Br 4-Nitrophenyl 31 I4-Nitrophenyl 32 CH₃ 4-Nitrophenyl 33 Cl 4-Tolyl 34 Br 4-Tolyl 35 I4-Tolyl 36 CH₃ 4-Tolyl 37 Cl 5-Chloro-2-fluorophenyl 38 Br5-Chloro-2-fluorophenyl 39 I 5-Chloro-2-fluorophenyl 40 CH₃5-Chloro-2-fluorophenyl 41 Cl 2-Chloro-4-nitrophenyl 42 Br2-Chloro-4-nitrophenyl 43 I 2-Chloro-4-nitrophenyl 44 CH₃2-Chloro-4-nitrophenyl 45 Cl 4-Trifluoromethylphenyl 46 Br4-Trifluoromethylphenyl 47 I 4-Trifluoromethylphenyl 48 CH₃4-Trifluoromethylphenyl 49 Cl 4-Fluoro-3-trifluoromethylphenyl 50 Br4-Fluoro-3-trifluoromethylphenyl 51 I 4-Fluoro-3-trifluoromethylphenyl52 CH₃ 4-Fluoro-3-trifluoromethylphenyl 53 Cl 2-Trifluoromethoxyphenyl54 Br 2-Trifluoromethoxyphenyl 55 I 2-Trifluoromethoxyphenyl 56 CH₃2-Trifluoromethoxyphenyl 57 Cl 2-Methoxyphenyl 58 Br 2-Methoxyphenyl 59I 2-Methoxyphenyl 60 CH₃ 2-Methoxyphenyl 61 Cl 4-Fluorophenyl 62 Br4-Fluorophenyl 63 I 4-Fluorophenyl 64 CH₃ 4-Fluorophenyl 65 Cl2-Fluorophenyl 66 Br 2-Fluorophenyl 67 I 2-Fluorophenyl 68 CH₃2-Fluorophenyl 69 Cl 2-Trifluoromethylphenyl 70 Br2-Trifluoromethylphenyl 71 I 2-Trifluoromethylphenyl 72 CH₃2-Trifluoromethylphenyl 73 Cl 2-Tolyl 74 Br 2-Tolyl 75 I 2-Tolyl 76 CH₃2-Tolyl 77 Cl 2-Chloro-4-fluorophenyl 78 Br 2-Chloro-4-fluorophenyl 79 I2-Chloro-4-fluorophenyl 80 CH₃ 2-Chloro-4-fluorophenyl 81 Cl2,3-Difluorophenyl 82 Br 2,3-Difluorophenyl 83 I 2,3-Difluorophenyl 84CH₃ 2,3-Difluorophenyl 85 Cl 2,4-Difluorophenyl 86 Br 2,4-Difluorophenyl87 I 2,4-Difluorophenyl 88 CH₃ 2,4-Difluorophenyl 89 Cl2-Fluoro-4-trifluoromethylphenyl 90 Br 2-Fluoro-4-trifluoromethylphenyl91 I 2-Fluoro-4-trifluoromethylphenyl 92 CH₃2-Fluoro-4-trifluoromethylphenyl 93 Cl 4-Fluoro-2-methylphenyl 94 Br4-Fluoro-2-methylphenyl 95 I 4-Fluoro-2-methylphenyl 96 CH₃4-Fluoro-2-methylphenyl 97 Cl 4-Trifluoromethoxyphenyl 98 Br4-Trifluoromethoxyphenyl 99 I 4-Trifluoromethoxyphenyl 100 CH₃4-Trifluoromethoxyphenyl 101 Cl 4-Fluoro-2-trifluoromethylphenyl 102 Br4-Fluoro-2-trifluoromethylphenyl 103 I 4-Fluoro-2-trifluoromethylphenyl104 CH₃ 4-Fluoro-2-trifluoromethylphenyl 105 Cl2-Fluoro-5-trifluoromethylphenyl 106 Br 2-Fluoro-5-trifluoromethylphenyl107 I 2-Fluoro-5-trifluoromethylphenyl 108 CH₃2-Fluoro-5-trifluoromethylphenyl 109 Cl 4-Cyano-2-methylphenyl 110 I4-Cyano-2-methylphenyl 111 Br 4-Cyano-2-methylphenyl 112 CH₃4-Cyano-2-methylphenyl

Table A1 describes compounds (A1.1 to A1.112) of the structure (I),where Y and Q have the values indicated in table A (line 1 to 112) andX1 is hydrogen, X2 is hydrogen and R is hydrogen.

Table A2 describes compounds (A2.1 to A2.112) of the structure (I),where Y and Q have the values indicated in table A (line 1 to 112) andX1 is hydrogen, X2 is hydrogen and R is methyl.

Table A3 describes compounds (A3.1 to A3.112) of the structure (I),where Y and Q have the values indicated in table A (line 1 to 112) andX1 is hydrogen, X2 is hydrogen and R is ethyl.

Table A4 describes compounds (A4.1 to A4.112) of the structure (I),where Y and Q have the values indicated in table A (line 1 to 112) andX1 is fluorine, X2 is hydrogen and R is hydrogen.

Table A5 describes compounds (A5.1 to A5.112) of the structure (I),where Y and Q have the values indicated in table A (line 1 to 112) andX1 is fluorine, X2 is hydrogen and R is methyl.

Table A6 describes compounds (A6.1 to A6.112) of the structure (I),where Y and Q have the values indicated in table A (line 1 to 112) andX1 is fluorine, X2 is hydrogen and R is ethyl.

Table A7 describes compounds (A7.1 to A7.112) of the structure (I),where Y and Q have the values indicated in table A (line 1 to 112) andX1 is methoxy, X2 is hydrogen and R is hydrogen.

Table A8 describes compounds (A8.1 to A8.112) of the structure (I),where Y and Q have the values indicated in table A (line 1 to 112) andX1 is methoxy, X2 is hydrogen and R is methyl.

Table A9 describes compounds (A9.1 to A9.112) of the structure (I),where Y and Q have the values indicated in table A (line 1 to 112) andX1 is methoxy, X2 is hydrogen and R is ethyl.

Table A10 describes compounds (A10.1 to A10.112) of the structure (I),where Y and Q have the values indicated in table A (line 1 to 112) andX1 is hydrogen, X2 is cyano and R is hydrogen.

Table A11 describes compounds (A11.1 to A11.112) of the structure (I),where Y and Q have the values indicated in table A (line 1 to 112) andX1 is hydrogen, X2 is cyano and R is methyl.

Table A12 describes compounds (A12.1 to A12.112) of the structure (I),where Y and Q have the values indicated in table A (line 1 to 112) andX1 is hydrogen, X2 is cyano and R is ethyl.

Structures of formula (III)

Table X of acetanilides of the structure (III) Line n^(o) Y 1 Cl 2 Br 3I 4 CH₃ 5 CF₃ 6 CHF₂ 7 OCF₃ 8 OCH₃ 9 OCHF₂

The compounds of the invention may be made by a variety of methods, forexample, the methods disclosed in WO 08/000438 or WO 2010/127928.

1) Compounds of formula (I) may be made by treatment of compounds offormula (IV), wherein X₁, X₂, Y and R are as defined for formula (I)with a compound of formula (V), wherein Q is as defined for formula (I)and R₂ is OH, C₁-C₆alkoxy, Cl, F, Br or I. When R₂ is OH, such reactionsmay be carried out in the presence of a coupling reagent, such as DCC(N,N′-dicyclohexylcarbodiimide), EDC(1-ethyl-3-[3-dimethylamino-propyl]carbodiimide hydrochloride) or BOP—Cl(bis(2-oxo-3-oxazolidinyl)phosphonic chloride), in the presence of abase, such as pyridine, triethylamine, 4-(dimethylamino)pyridine ordiisopropylethylamine, and optionally in the presence of a nucleophiliccatalyst, such as hydroxybenzotriazole. When R₂ is Cl, such reactionsmay be carried out under basic conditions, for example in the presenceof pyridine, triethylamine, 4-(dimethylamino)pyridine ordiisopropylethylamine, and optionally in the presence of a nucleophiliccatalyst. Alternatively, a catalytic quantity of a iodide salt, forexample potassium iodide, can be added to the acid chloride in an inertsolvent, such as acetonitrile, to yield the product (see for exampleOrganic Letters, 15 (3), pp. 702-705, 2013). In a further alternative,the reaction may be conducted in a biphasic system comprising an organicsolvent, preferably ethyl acetate, and an aqueous solvent, preferably asolution of sodium bicarbonate. When R₂ is C₁-C₆alkoxy the ester may beconverted directly to the amide by heating the ester and amine togetherin a thermal process.

2) Acid halides of formula (V), wherein R₂ is Cl, F or Br, may be madefrom carboxylic acids of formula (V), wherein R₂ is OH by treatment withthionyl chloride or oxalyl chloride or by treatment with phosphorylbromide or with cyanuryl fluoride.

3) Carboxylic acids of formula (V), wherein R₂ is OH, may be formed fromesters of formula (V), wherein R₂ is C₁-C₆alkoxy by treatment of theester with an alkali hydroxide, such as sodium hydroxide, in a solvent,such as ethanol.

4) Esters of formula (V), wherein R₂ is C₁-C₆alkoxy, may be made bytreatment of R_(2a)—OH wherein R_(2a) is C₁-C₆alkyl, by acylation with acarboxylic acid of formula Q-COOH or an acid halide of formula Q-COHal,wherein Hal is Cl, F or Br, under standard conditions as described in1).

5) Compounds of formula (IV) with R different from hydrogen, wherein X₁,X₂ and Y are as defined for formula (I) can be made by formation of theN—R bond. For example, reductive amination may be achieved by treatmentof the aniline (IVa) with an aldehyde or ketone and a reducing agentsuch as sodium cyanoborohydride. Alternatively, alkylation may beachieved by treating the amine (IVa) with an alkylating agent such as analkyl halide, optionally in the presence of a base.

6) Compounds of formula (IVa), wherein X₁, X₂ and Y are as defined forformula (I), can be made from compounds of formula (VI) by reduction ofthe —NO₂ function under a variety of conditions generally well known,for example reduction using hydrogen and a metal- or metal oxide-basedcatalyst, like palladium, in a compatible solvent. The reaction can beperformed in a broad range of temperatures, preferably between −30° C.and 150° C., most preferably 10° C. to 50° C., and pressures, preferablybetween atmospheric pressure and 200 atm, most preferably below 10 atm.A further method for the reduction of an aromatic nitro group to aminogroup uses SnCl₂ in a protic solvent, in presence of an acid. A furthermethod uses a metal, like iron, as reducing agent and an acid like HCl,acetic acid or NH₄Cl.

7) Compounds of formula (VI), wherein X₁ is OMe and X₂ and Y are asdefined for formula (I), may be made by substitution of the fluorineatom of the compounds of formula (VI), wherein X₁ is F and X₂ and Y areas defined for formula (I) by, for example, treating it in methylalcohol, preferably in presence of a base, like potassium carbonate.

8) Compounds of formula (VI), wherein X₁, X₂ and Y are as defined forformula (I), can be prepared by reacting compounds of formula (VII),wherein Y is as defined for formula (I) and compounds of formula (VIII),wherein X₁ and X₂ are as defined for formula (I) and wherein R₃ is OH,Cl, F, Br or I. When R₃ is OH, such reactions may be carried out in thepresence of a coupling reagent, such as DCC(N,N′-dicyclohexylcarbodiimide), EDC(1-ethyl-3-[3-dimethylamino-propyl]carbodiimide hydrochloride) or BOP—Cl(bis(2-oxo-3-oxazolidinyl)phosphonic chloride), in the presence of abase, such as pyridine, triethylamine, 4-(dimethylamino)pyridine ordiisopropylethylamine, and optionally in the presence of a nucleophiliccatalyst, such as hydroxybenzotriazole. When R₃ is Cl, such reactionsmay be carried out under basic conditions, for example in the presenceof pyridine, triethylamine, 4-(dimethylamino)pyridine ordiisopropylethylamine, or preferably non-basic conditions, andoptionally in the presence of a nucleophilic catalyst. Compounds of theformula (VIII) are commercially available.

9) Compounds of formula (VII), wherein Y is as defined for formula (I),can be prepared by reacting compounds of formula (IX) with a compound offormula (X), wherein Z is I or Br, in analogy to WO 2011009540. Thecompounds (X) are easily accessible.

10) Compounds of formula (IX), wherein Y is as defined for formula (I),may be prepared by reducing the nitro function of compounds of formula(XI), wherein Y is as defined for formula (I), using standard methods.Compounds of formula (XI) can be made by difluoromethylation ofcompounds of formula (XII). Many compounds of formula (XII) aredescribed in the literature or can be made in an analogous way.

11) Alternatively, compounds of formula (VII), wherein Y is chlorine,bromine or iodine, can be prepared by reacting compound of formula(XIII), described in WO 2011009540, with an halogenating reagent like,for example with N-chlorosuccinimide (NCS), N-bromosuccinimide (NBS) orN-iodosuccinimide (NIS).

12) Compounds of formula (I) may be also be made by treatment ofcompounds of formula (XIV), wherein Q, X₁, X₂ and R are as defined forformula (I) and R₄ is OH, Cl, F, Br or I with a compound of formula(VII), wherein Y is as defined for formula (I). When R₄ is OH, suchreactions may be carried out in the presence of a coupling reagent, suchas DCC (N,N′-dicyclohexylcarbodiimide), EDC(1-ethyl-3-[3-dimethylamino-propyl]carbodiimide hydrochloride) or BOP—Cl(bis(2-oxo-3-oxazolidinyl)phosphonic chloride), in the presence of abase, such as pyridine, triethylamine, 4-(dimethylamino)pyridine ordiisopropylethylamine, and optionally in the presence of a nucleophiliccatalyst, such as hydroxybenzotriazole. When R₄ is Cl, such reactionsmay be carried out under basic conditions, for example in the presenceof pyridine, triethylamine, 4-(dimethylamino)pyridine ordiisopropylethylamine, and optionally in the presence of a nucleophiliccatalyst, or under non-basic conditions.

13) Alternatively, compounds of formula (I) may be also be made bytreatment of compounds of formula (XIV), wherein Q, X₁, X₂ and R are asdefined for formula (I) and R₄ is Cl, F, Br or I, with a compound offormula (III), wherein Y is as defined for formula (I). Such reactionsmay be carried out under basic conditions, for example in the presenceof pyridine, triethylamine, 4-(dimethylamino)pyridine ordiisopropylethylamine, and optionally in the presence of a nucleophiliccatalyst. The imide intermediate may or may not be isolated and mayconveniently be hydrolysed under mild alkaline conditions duringwork-up.

14) Compounds of formula (III), wherein Y is as defined for formula (I),can be prepared from compounds of formula (VII), wherein Y is as definedfor formula (I), by treatment with an activated form of acetic acid,like acetic anhydride or acetyl chloride.

15) Compounds of formula (XIV) may be made by treatment of compounds offormula (XVI), wherein X₁, X₂ and R are as defined for formula (I) andR₅ is C₁-C₆ alkoxy, with a compound of formula (V), wherein Q is asdefined for formula (I) and R₂ is OH, C₁-C₆alkoxy, Cl, F, Br or I. WhenR₂ is OH, such reactions may be carried out in the presence of acoupling reagent, such as DCC (N,N′-dicyclohexylcarbodiimide), EDC(1-ethyl-3-[3-dimethylamino-propyl]carbodiimide hydrochloride) or BOP—Cl(bis(2-oxo-3-oxazolidinyl)phosphonic chloride), in the presence of abase, such as pyridine, triethylamine, 4-(dimethylamino)pyridine ordiisopropylethylamine, and optionally in the presence of a nucleophiliccatalyst, such as hydroxybenzotriazole. When R₂ is Cl, such reactionsmay be carried out under basic conditions, for example in the presenceof pyridine, triethylamine, 4-(dimethylamino)pyridine ordiisopropylethylamine, and optionally in the presence of a nucleophiliccatalyst. Alternatively, the reaction may be conducted in a biphasicsystem comprising an organic solvent, preferably ethyl acetate, and anaqueous solvent, preferably a solution of sodium bicarbonate. When R₂ isC₁-C₆ alkoxy the ester may be converted directly to the amide by heatingthe ester and amine together in a thermal process. In compounds offormula (XIV), the group R₄ can be changed from C₁-C₆ alkoxy to OH byhydrolysis of the ester function with a base, like LiOH, theneventually, to chloride, with thionyl chloride or oxalyl chloride.

16) Compounds of formula (XVI) wherein X₁, X₂ and R are as defined forformula (I) and R₅ is C₁-C₆ alkoxy may be made by reducing the nitrofunction of compounds of formula (XVII) wherein X₁ and X₂ are as definedfor formula (I) and R₅ is C₁-C₆ alkoxy, and submitting the aniline toreductive amination for compounds of the formula (XVI) with R differentfrom hydrogen. Compounds of formula (XVII) are known or can be made byanalogy by somebody skilled in the art.

17) Compounds of formula (I), wherein X₁, X₂, Y and R are as defined forformula (I) and where Q is Q₃ or Q₅ may also be obtained by treatment ofcompounds of formula (I), wherein X₁, X₂, Y and R are as defined forformula (I) with Q is Q₂ or Q₄, respectively, by treatment with anoxidizing agent, like a peroxyacid, m-chloroperbenzoic acid, forexample.

The compounds according to the invention, namely the compounds offormula (I) and (III), and the compounds mentioned in the methodaccording to the invention may exist in different geometric or opticalisomers or tautomeric forms.

This invention covers all such isomers and tautomers and mixturesthereof in all proportions as well as isotopic forms such as deuteratedcompounds.

The invention also covers salts of all compounds of the invention.

The compounds of formula (I) can be used to combat and controlinfestations of insect pests such as Lepidoptera, Diptera, Hemiptera,Thysanoptera, Orthoptera, Dictyoptera, Coleoptera, Siphonaptera,Hymenoptera and Isoptera and also other invertebrate pests, for example,acarine, nematode and mollusc pests. Insects, acarines, nematodes andmolluscs are hereinafter collectively referred to as pests. The pestswhich may be combated and controlled by the use of the inventioncompounds include those pests associated with agriculture (which termincludes the growing of crops for food and fiber products), horticultureand animal husbandry, companion animals, forestry and the storage ofproducts of vegetable origin (such as fruit, grain and timber); thosepests associated with the damage of man-made structures and thetransmission of diseases of man and animals; and also nuisance pests(such as flies). Examples of the abovementioned animal pests are:

from the order Acarina, for example,

Acalitus spp., Aculus spp., Acaricalus spp., Aceria spp., Acarus siro,Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobiaspp., Calipitrimerus spp., Chorioptes spp., Dermanyssus gallinae,Dermatophagoides spp., Eotetranychus spp., Eriophyes spp.,Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Olygonychus spp.,Ornithodoros spp., Polyphagotarsone latus, Panonychus spp.,Phyllocoptruta oleivora, Phytonemus spp., Polyphagotarsonemus spp.,Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp.,Steneotarsonemus spp., Tarsonemus spp., and Tetranychus spp.;

from the order Anoplura, for example,

Haematopinus spp., Linognathus spp., Pediculus spp., Pemphigus spp., andPhylloxera spp.;

from the order Coleoptera, for example,

Agriotes spp., Amphimallon majale, Anomala orientalis, Anthonomus spp.,Aphodius spp., Astylus atromaculatus, Ataenius spp., Atomaria linearis,Chaetocnema tibialis, Cerotoma spp., Conoderus spp., Cosmopolites spp.,Cotinis nitida, Curculio spp., Cyclocephala spp., Dermestes spp.,Diabrotica spp., Diloboderus abderus, Epilachna spp., Eremnus spp.,Heteronychus arator, Hypothenemus hampei, Lagria vilosa, LeptinotarsadecemLineata, Lissorhoptrus spp., Liogenys spp., Maecolaspis spp.,Maladera castanea, Megascelis spp., Melighetes aeneus, Melolontha spp.,Myochrous armatus, Orycaephilus spp., Otiorhynchus spp., Phyllophagaspp., Phlyctinus spp., Popillia spp., Psylliodes spp., Rhyssomatusaubtilis, Rhizopertha spp., Scarabeidae, Sitophilus spp., Sitotrogaspp., Somaticus spp., Sphenophorus spp., Sternechus subsignatus,Tenebrio spp., Tribolium spp., and Trogoderma spp.;

from the order Diptera, for example,

Aedes spp., Anopheles spp., Antherigona soccata, Bactrocea oleae, Bibiohortulanus, Bradysia spp., Calliphora erythrocephala, Ceratitis spp.,Chrysomyia spp., Culex spp., Cuterebra spp., Dacus spp., Delia spp.,Drosophila melanogaster, Fannia spp., Gastrophilus spp., Geomyzatripunctata, Glossina spp., Hypoderma spp., Hyppobosca spp., Liriomyzaspp., Lucilia spp., Melanagromyza spp., Musca spp., Oestrus spp.,Orseolia spp., Oscinella frit, Pegomyia hyoscyami, Phorbia spp.,Rhagoletis spp., Rivelia quadrifasciata, Scatella spp., Sciara spp.,Stomoxys spp., Tabanus spp., Tannia spp., and Tipula spp.;

from the order Hemiptera, for example,

Acanthocoris scabrator, Acrosternum spp., Adelphocoris lineolatus,Amblypelta nitida, Bathycoelia thalassina, Blissus spp., Cimex spp.,Clavigralla tomentosicollis, Creontiades spp., Distantiella theobroma,Dichelops furcatus, Dysdercus spp., Edessa spp., Euchistus spp.,Eurydema pulchrum, Eurygaster spp., Halyomorpha halys, Horciasnobilellus, Leptocorisa spp., Lygus spp., Margarodes spp., Murgantiahistrionic, Neomegalotomus spp., Nesidiocoris tenuis, Nezara spp.,Nysius simulans, Oebalus insularis, Piesma spp., Piezodorus spp.,Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea,Scotinophara spp., Thyanta spp., Triatoma spp., Vatiga illudens;

Acyrthosium pisum, Adalges spp., Agalliana ensigera, Agonoscenatargionii, Aleurodicus spp., Aleurocanthus spp., Aleurolobus barodensis,Aleurothrixus floccosus, Aleyrodes brassicae, Amarasca biguttula,Amritodus atkinsoni, Aonidiella spp., Aphididae, Aphis spp., Aspidiotusspp., Aulacorthum solani, Bactericera cockerelli, Bemisia spp.,Brachycaudus spp., Brevicoryne brassicae, Cacopsylla spp., Cavariellaaegopodii Scop., Ceroplaster spp., Chrysomphalus aonidium, Chrysomphalusdictyospermi, Cicadella spp., Cofana spectra, Cryptomyzus spp.,Cicadulina spp., Coccus hesperidum, Dalbulus maidis, Dialeurodes spp.,Diaphorina citri, Diuraphis noxia, Dysaphis spp., Empoasca spp.,Eriosoma larigerum, Erythroneura spp., Gascardia spp., Glycaspisbrimblecombei, Hyadaphis pseudobrassicae, Hyalopterus spp., Hyperomyzuspallidus, Idioscopus clypealis, Jacobiasca lybica, Laodelphax spp.,Lecanium corni, Lepidosaphes spp., Lopaphis erysimi, Lyogenys maidis,Macrosiphum spp., Mahanarva spp., Metcalfa pruinosa, Metopolophiumdirhodum, Myndus crudus, Myzus spp., Neotoxoptera spp., Nephotettixspp., Nilaparvata spp., Nippolachnus pini Mats, Odonaspis ruthae, Oregmalanigera Zehnter, Parabemisia myricae, Paratrioza cockerelli, Parlatoriaspp., Pemphigus spp., Peregrinus maidis, Perkinsiella spp., Phorodonhumuli, Phylloxera spp., Planococcus spp., Pseudaulacaspis spp.,Pseudococcus spp., Pseudatomoscelis seriatus, Psylla spp., Pulvinariaaethiopica, Quadraspidiotus spp., Quesada gigas, Recilia dorsalis,Rhopalosiphum spp., Saissetia spp., Scaphoideus spp., Schizaphis spp.,Sitobion spp., Sogatella furcifera, Spissistilus festinus, TarophagusProserpina, Toxoptera spp., Trialeurodes spp., Tridiscus sporoboli,Trionymus spp., Trioza erytreae, Unaspis citri, Zygina flammigera,Zyginidia scutellaris;

from the order Hymenoptera, for example,

Acromyrmex, Arge spp., Atta spp., Cephus spp., Diprion spp.,Diprionidae, Gilpinia polytoma, Hoplocampa spp., Lasius spp., Monomoriumpharaonis, Neodiprion spp., Pogonomyrmex spp., Slenopsis invicta,Solenopsis spp., and Vespa spp.;

from the order Isoptera, for example, Coptotermes spp., Corniternescumulans, Incisitermes spp., Macrotermes spp., Mastotermes spp.,Microtermes spp., Reticulitermes spp.; Solenopsis geminate

from the order Lepidoptera, for example,

Acleris spp., Adoxophyes spp., Aegeria spp., Agrotis spp., Alabamaargillaceae, Amylois spp., Anticarsia gemmatalis, Archips spp.,Argyresthia spp., Argyrotaenia spp., Autographa spp., Bucculatrixthurberiella, Busseola fusca, Cadra cautella, Carposina nipponensis,Chilo spp., Choristoneura spp., Chrysoteuchia topiaria, Clysiaambiguella, Cnaphalocrocis spp., Cnephasia spp., Cochylis spp.,Coleophora spp., Colias lesbia, Cosmophila flava, Crambus spp.,Crocidolomia binotalis, Cryptophlebia leucotreta, Cydalima perspectalis,Cydia spp., Diaphania perspectalis, Diatraea spp., Diparopsis castanea,Earias spp., Eldana saccharina, Ephestia spp., Epinotia spp., Estigmeneacrea, Etiella zinckinella, Eucosma spp., Eupoecilia ambiguella,Euproctis spp., Euxoa spp., Feltia jaculiferia, Grapholita spp., Hedyanubiferana, Heliothis spp., Hellula undalis, Herpetogramma spp.,Hyphantria cunea, Keiferia lycopersicella, Lasmopalpus lignosellus,Leucoptera scitella, Lithocollethis spp., Lobesia botrana, Loxostegebifidalis, Lymantria spp., Lyonetia spp., Malacosoma spp., Mamestrabrassicae, Manduca sexta, Mythimna spp., Noctua spp., Operophtera spp.,Orniodes indica, Ostrinia nubilalis, Pammene spp., Pandemis spp.,Panolis flammea, Papaipema nebris, Pectinophora gossypiela,Perileucoptera coffeella, Pseudaletia unipuncta, Phthorimaeaoperculella, Pieris rapae, Pieris spp., Plutella xylostella, Prays spp.,Pseudoplusia spp., Rachiplusia nu, Richia albicosta, Scirpophaga spp.,Sesamia spp., Sparganothis spp., Spodoptera spp., Sylepta derogate,Synanthedon spp., Thaumetopoea spp., Tortrix spp., Trichoplusia ni, Tutaabsoluta, and Yponomeuta spp.;

from the order Mallophaga, for example,

Damalinea spp., and Trichodectes spp.;

from the order Orthoptera, for example,

Blatta spp., Blattella spp., Gryllotalpa spp., Leucophaea maderae,Locusta spp., Neocurtilla hexadactyla, Periplaneta spp., Scapteriscusspp., and Schistocerca spp.;

from the order Psocoptera, for example,

Liposcelis spp.;

from the order Siphonaptera, for example,

Ceratophyllus spp., Ctenocephalides spp., and Xenopsylla cheopis;

from the order Thysanoptera, for example,

Calliothrips phaseoli, Frankliniella spp., Heliothrips spp.,Hercinothrips spp., Parthenothrips spp., Scirtothrips aurantii,Sericothrips variabilis, Taeniothrips spp., Thrips spp.;

from the order Thysanura, for example,

Lepisma saccharina.

The active ingredients according to the invention can be used forcontrolling, i.e. containing or destroying, pests of the abovementionedtype which occur in particular on plants, especially on useful plantsand ornamentals in agriculture, in horticulture and in forests, or onorgans, such as fruits, flowers, foliage, stalks, tubers or roots, ofsuch plants, and in some cases even plant organs which are formed at alater point in time remain protected against these pests.

Suitable target crops are, in particular, cereals, such as wheat,barley, rye, oats, rice, maize or sorghum; beet, such as sugar or fodderbeet; fruit, for example pomaceous fruit, stone fruit or soft fruit,such as apples, pears, plums, peaches, almonds, cherries or berries, forexample strawberries, raspberries or blackberries; leguminous crops,such as beans, lentils, peas or soya; oil crops, such as oilseed rape,mustard, poppies, olives, sunflowers, coconut, castor, cocoa or groundnuts; cucurbits, such as pumpkins, cucumbers or melons; fibre plants,such as cotton, flax, hemp or jute; citrus fruit, such as oranges,lemons, grapefruit or tangerines; vegetables, such as spinach, lettuce,asparagus, cabbages, carrots, onions, tomatoes, potatoes or bellpeppers; Lauraceae, such as avocado, Cinnamonium or camphor; and alsotobacco, nuts, coffee, eggplants, sugarcane, tea, pepper, grapevines,hops, the plantain family, latex plants and ornamentals.

The invention therefore provides a method of combating and controllinginsects, acarines, nematodes or molluscs which comprises applying aninsecticidally, acaricidally, nematicidally or molluscicidally effectiveamount of a compound of formula (I), or a composition containing acompound of formula (I), to a pest, a locus of pest, preferably a plant,or to a plant susceptible to attack by a pest, The compounds of formula(I) are preferably used against insects, acarines or nematodes.

As for acari, for example, Tetranychus cinnabarinus, Tetranychusurticae, Panonychus citri, Aculops pelekassi, Tarsonemus spp.

As for nematodes, for example, Meloidogyne incognita, Bursaphelenchuslignicolus Mamiya et Kiyohara, Aphelenchoides besseyi, Heteroderaglycines, Pratylenchus spp.

Additionally, the compounds can be used for controlling animal pests, inparticular insects, arachnids, helminths, nematodes and molluscs, whichare encountered in agriculture, in horticulture, the field of veterinarymedicine, in forests, in gardens and leisure facilities, in theprotection of stored products and of materials, and in the hygienesector. They may preferably be employed as plant protection agents. Theymay be active against normally sensitive and resistant species andagainst all or some stages of development.

These pests include inter alia:

From the order of the Anoplura (Phthiraptera), for example, Damaliniaspp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectesspp.

From the class of the Arachnida, for example, Acarus siro, Aceriasheldoni, Aculops spp., Aculus spp., Amblyomma spp., Argas spp.,Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp.,Dermanyssus gallinae, Eotetranychus spp., Epitrimerus pyri,Eutetranychus spp., Eriophyes spp., Hemitarsonemus spp., Hyalomma spp.,Ixodes spp., Latrodectus mactans, Metatetranychus spp., Oligonychusspp., Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora,Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp.,Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp.,Tarsonemus spp., Tetranychus spp., Vasates lycopersici.

From the class of the Bivalva, for example, Dreissena spp.

From the order of the Chilopoda, for example, Geophilus spp., Scutigeraspp.

From the order of the Coleoptera, for example, Acanthoscehdes obtectus,Adoretus spp., Agelastica alni, Agriotes spp., Amphimallon solstitialis,Anobium punctatum, Anoplophora spp., Anthonomus spp., Anthrenus spp.,Apogonia spp., Atomaria spp., Attagenus spp., Bruchidius obtectus,Bruchus spp., Ceuthorhynchus spp., Cleonus mendicus, Conoderus spp.,Cosmopolites spp., Costelytra zealandica, Curculio spp., Cryptorhynchuslapathi, Dermestes spp., Diabrotica spp., Epilachna spp., Faustinuscubae, Gibbium psylloides, Heteronychus arator, Hylamorpha elegans,Hylotrupes bajulus, Hypera postica, Hypothenemus spp., Lachnosternaconsanguinea, Leptinotarsa decemlineata, Lissorhoptrus oryzophilus,Lixus spp., Lyctus spp., Meligethes aeneus, Melolontha melolontha,Migdolus spp., Monochamus spp., Naupactus xanthographus, Niptushololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Otiorrhynchussulcatus, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp.,Popillia japonica, Premnotrypes spp., Psylliodes chrysocephala, Ptinusspp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp.,Sphenophorus spp., Sternechus spp., Symphyletes spp., Tenebrio molitor,Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrusspp.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Bibio hortulanus, Calliphora erythrocephala, Ceratitis capitata,Chrysomyia spp., Cochliomyia spp., Cordylobia anthropophaga, Culex spp.,Cuterebra spp., Dacus oleae, Dermatobia hominis, Drosophila spp., Fanniaspp., Gastrophilus spp., Hylemyia spp., Hyppobosca spp., Hypoderma spp.,Liriomyza spp., Lucilia spp., Musca spp., Nezara spp., Oestrus spp.,Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Stomoxys spp., Tabanusspp., Tannia spp., Tipula paludosa, Wohlfahrtia spp.

From the class of the Gastropoda, for example, Anion spp., Biomphalariaspp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp.,Oncomelania spp., Succinea spp.

From the class of the helminths, for example, Ancylostoma duodenale,Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp.,Ascaris lumbricoides, Ascaris spp., Brugia malayi, Brugia timori,Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp.,Dicrocoelium spp., Dictyocaulus filaria, Diphyllobothrium latum,Dracunculus medinensis, Echinococcus granulosus, Echinococcusmultilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp.,Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa,Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocercavolvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp.,Strongyloides fuelleborni, Strongyloides stercoralis, Stronyloides spp.,Taenia saginata, Taenia solium, Trichinella spiralis, Trichinellanativa, Trichinella britovi, Trichinella nelsoni, Trichinellapseudopsiralis, Trichostrongulus spp., Trichuris trichiura, Wuchereriabancrofti.

It may be furthermore possible to control protozoa, such as Eimeria.

From the order of the Heteroptera, for example, Anasa tristis,Antestiopsis spp., Blissus spp., Calocoris spp., Campylomma livida,Cavelerius spp., Cimex spp., Creontiades dilutus, Dasynus piperis,Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistusspp., Eurygaster spp., Heliopeltis spp., Horcias nobilellus, Leptocorisaspp., Leptoglossus phyllopus, Lygus spp., Macropes excavatus, Miridae,Nezara spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp.,Psallus seriatus, Pseudacysta persea, Rhodnius spp., Sahlbergellasingularis, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatomaspp. From the order of the Homoptera, for example, Acyrthosipon spp.,Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobusbarodensis, Aleurothrixus spp., Amrasca spp., Anuraphis cardui,Aonidiella spp., Aphanostigma pini, Aphis spp., Arboridia apicalis,Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthum solani,Bemisia spp., Brachycaudus helichrysii, Brachycolus spp., Breviconynebrassicae, Calligypona marginata, Carneocephala fulgida, Ceratovacunalanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii,Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola,Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp.,Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp., Diaphorina spp.,Diaspis spp., Dorsalis spp., Drosicha spp., Dysaphis spp., Dysmicoccusspp., Empoasca spp., Eriosoma spp., Erythroneura spp., Euscelisbilobatus, Geococcus coffeae, Homalodisca coagulata, Hyalopterusarundinis, Icerya spp., Idiocerus spp., Idioscopus spp., Laodelphaxstriatellus, Lecanium spp., Lepidosaphes spp., Lipaphis erysimi,Macrosiphum spp., Mahanarva fimbriolata, Melanaphis sacchari,Metcalfiella spp., Metopolophium dirhodum, Monellia costalis,Monelliopsis pecanis, Myzus spp., Nasonovia ribisnigri, Nephotettixspp., Nilaparvata lugens, Oncometopia spp., Orthezia praelonga,Parabemisia myricae, Paratrioza spp., Parlatoria spp., Pemphigus spp.,Peregrinus maidis, Phenacoccus spp., Phloeomyzus passerinii, Phorodonhumuli, Phylloxera spp., Pinnaspis aspidistrae, Planococcus spp.,Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcusspp., Psylla spp., Pteromalus spp., Pyrilla spp., Quadraspidiotus spp.,Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., Saissetia spp.,Scaphoides titanus, Schizaphis graminum, Selenaspidus articulatus,Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina,Tenalaphara malayensis, Tinocallis caryaefoliae, Tomaspis spp.,Toxoptera spp., Trialeurodes vaporariorum, Trioza spp., Typhlocyba spp.,Unaspis spp., Viteus vitifolii.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Mono-morium pharaonis, Vespa spp.

From the order of the Isopoda, for example, Armadillidium vulgare,Oniscus asellus, Porcellio scaber.

From the order of the Isoptera, for example, Reticulitermes spp.,Odontotermes spp.

From the order of the Lepidoptera, for example, Acronicta major, Aedialeucomelas, Agrotis spp., Alabama argillacea, Anticarsia spp., Barathrabrassicae, Bucculatrix thurberiella, Bupalus piniarius, Cacoecia podana,Capua reticulana, Carpocapsa pomonella, Cheimatobia brumata, Chilo spp.,Choristoneura fumiferana, Clysia ambiguella, Cnaphalocerus spp., Eariasinsulana, Ephestia kuehniella, Euproctis chrysorrhoea, Euxoa spp.,Feltia spp., Galleria mellonella, Helicoverpa spp., Heliothis spp.,Hofmannophila pseudospretella, Homona magnanima, Hyponomeuta padella,Laphygma spp., Lithocolletis blancardella, Lithophane antennata,Loxagrotis albicosta, Lymantria spp., Malacosoma neustria, Mamestrabrassicae, Mocis repanda, Mythimna separata, Oria spp., Oulema oryzae,Panolis flammea, Pectinophora gossypiella, Phyllocnistis citrella,Pieris spp., Plutella xylostella, Prodenia spp., Pseudaletia spp.,Pseudoplusia includens, Pyrausta nubilalis, Spodoptera spp., Thermesiagemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana,Trichoplusia spp.

From the order of the Orthoptera, for example, Acheta domesticus, Blattaorientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae,Locusta spp., Melanoplus spp., Periplaneta americana, Schistocercagregaria.

From the order of the Siphonaptera, for example, Ceratophyllus spp.,Xenopsylla cheopis.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanoptera, for example, Baliothrips biformis,Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothripsfemoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothripsspp., Taeniothrips cardamoni, Thrips spp.

From the order of the Thysanura, for example, Lepisma saccharina.

The phytoparasitic nematodes include, for example, Anguina spp.,Aphelenchoides spp., Belonoaimus spp., Bursaphelenchus spp., Ditylenchusdipsaci, Globodera spp., Heliocotylenchus spp., Heterodera spp.,Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholussimilis, Rotylenchus spp., Trichodorus spp., Tylenchorhynchus spp.,Tylenchulus spp., Tylenchulus semipenetrans, Xiphinema spp.

Furthermore, in the field of veterinary medicine, the novel compounds ofthe present invention can be effectively used against various harmfulanimal parasitic pests (endoparasites and ectoparasites), for example,insects and helminthes.

Examples of such animal parasitic pests include the pests as describedbelow.

Examples of the insects include Gasterophilus spp., Stomoxys spp.,Trichodectes spp., Rhodnius spp., Ctenocephalides canis, Cimx lecturius,Ctenocephalides felis, Lucilia cuprina, and the like.

Examples of acari include Ornithodoros spp., Ixodes spp., Boophilusspp., and the like.

In the veterinary fields, e.g. in the field of veterinary medicine, theactive compounds according to the present invention are active againstanimal parasites, in particular ectoparasites or endoparasites.

The term endoparasites includes in particular helminths, such ascestodes, nematodes or trematodes, and protozoae, such as coccidia.

Ectoparasites are typically and preferably arthropods, in particularinsects such as flies (stinging and licking), parasitic fly larvae,lice, hair lice, bird lice, fleas and the like; or acarids, such asticks, for examples hard ticks or soft ticks, or mites, such as scabmites, harvest mites, bird mites and the like.

These parasites include:

From the order of the Anoplurida, for example Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.;particular examples are: Linognathus setosus, Linognathus vituli,Linognathus ovillus, Linognathus oviformis, Linognathus pedalis,Linognathus stenopsis, Haematopinus asini macrocephalus, Haematopinuseurysternus, Haematopinus suis, Pediculus humanus capitis, Pediculushumanus corporis, Phylloera vastatrix, Phthirus pubis, Solenopotescapillatus; from the order of the Mallophagida and the subordersAmblycerina and Ischnocerina, for example Trimenopon spp., Menopon spp.,Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp.,Damalina spp., Trichodectes spp., Felicola spp.; particular examplesare: Bovicola bovis, Bovicola ovis, Bovicola limbata, Damalina bovis,Trichodectes canis, Felicola subrostratus, Bovicola caprae, Lepikentronovis, Werneckiella equi; from the order of the Diptera and the subordersNematocerina and Brachycerina, for example Aedes spp., Anopheles spp.,Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyiaspp., Culicoides spp., Chrysops spp., Odagmia spp., Wilhelmia spp.,Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp.,Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxysspp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp.,Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp.,Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp.,Hippobosca spp., Lipoptena spp., Melophagus spp., Rhinoestrus spp.,Tipula spp.; particular examples are: Aedes aegypti, Aedes albopictus,Aedes taeniorhynchus, Anopheles gambiae, Anopheles maculipennis,Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus,Culex pipiens, Culex tarsalis, Fannia canicularis, Sarcophaga carnaria,Stomoxys calcitrans, Tipula paludosa, Lucilia cuprina, Lucilia sericata,Simulium reptans, Phlebotomus papatasi, Phlebotomus longipalpis, Odagmiaornata, Wilhelmia equina, Boophthora erythrocephala, Tabanus bromius,Tabanus spodopterus, Tabanus atratus, Tabanus sudeticus, Hybomitraciurea, Chrysops caecutiens, Chrysops relictus, Haematopota pluvialis,Haematopota italica, Musca autumnalis, Musca domestica, Haematobiairritans irritans, Haematobia irritans exigua, Haematobia stimulans,Hydrotaea irritans, Hydrotaea albipuncta, Chrysomya chloropyga,Chrysomya bezziana, Oestrus ovis, Hypoderma bovis, Hypoderma lineatum,Przhevalskiana silenus, Dermatobia hominis, Melophagus ovinus, Lipoptenacapreoli, Lipoptena cervi, Hippobosca variegate, Hippobosca equina,Gasterophilus intestinalis, Gasterophilus haemorroidalis, Gasterophilusinermis, Gasterophilus nasalis, Gasterophilus nigricornis, Gasterophiluspecorum, Braula coeca; from the order of the Siphonapterida, for examplePulex spp., Ctenocephalides spp., Tunga spp., Xenopsylla spp.,Ceratophyllus spp.; particular examples are: Ctenocephalides canis,Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsyllacheopis; from the order of the Heteropterida, for example Cimex spp.,Triatoma spp., Rhodnius spp., Panstrongylus spp.

From the order of the Blattarida, for example Blatta orientalis,Periplaneta americana, Blattela germanica, Supella spp., (e.g. Suppellalongipalpa);

From the subclass of the Acari (Acarina) and the orders of the Meta- andMesostigmata, for example Argas spp., Ornithodorus spp., Otobius spp.,Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp., Dermacentorspp., Haemophysalis spp., Hyalomma spp., Dermanyssus spp., Rhipicephalusspp., (the original genus of multi host ticks) Ornithonyssus spp.,Pneumonyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp.,Varroa spp., Acarapis spp.; particular examples are: Argas persicus,Argas reflexus, Ornithodorus moubata, Otobius megnini, Rhipicephalus(Boophilus) microplus, Rhipicephalus (Boophilus) decoloratus,Rhipicephalus (Boophilus) annulatus, Rhipicephalus (Boophilus)calceratus, Hyalomma anatolicum, Hyalomma aegypticum, Hyalommamarginatum, Hyalomma transiens, Rhipicephalus evertsi, Ixodes ricinus,Ixodes hexagonus, Ixodes canisuga, Ixodes pilosus, Ixodes rubicundus,Ixodes scapularis, Ixodes holocyclus, Haemaphysalis concinna,Haemaphysalis punctata, Haemaphysalis cinnabarine, Haemaphysalisotophila, Haemaphysalis leachi, Haemaphysalis longicorni, Dermacentormarginatus, Dermacentor reticulatus, Dermacentor pictus, Dermacentoralbipictus, Dermacentor andersoni, Dermacentor variabilis, Hyalommamauritanicum, Rhipicephalus sanguineus, Rhipicephalus bursa,Rhipicephalus appendiculatus, Rhipicephalus capensis, Rhipicephalusturanicus, Rhipicephalus zambeziensis, Amblyomma americanum, Amblyommavariegatum, Amblyomma maculatum, Amblyomma hebraeum, Amblyommacajennense, Dermanyssus gallinae, Ornithonyssus bursa, Ornithonyssussylviarum, Varroa jacobsoni; from the order of the Actinedida(Prostigmata) and Acaridida (Astigmata), for example Acarapis spp.,Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp.,Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp.,Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp.,Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp.,Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.;particular examples are: Cheyletiella yasguri, Cheyletiella blakei,Demodex canis, Demodex bovis, Demodex ovis, Demodex caprae, Demodexequi, Demodex caballi, Demodex suis, Neotrombicula autumnalis,Neotrombicula desaleri, Neoschongastia xerothermobia, Trombiculaakamushi, Otodectes cynotis, Notoedres cati, Sarcoptis canis, Sarcoptesbovis, Sarcoptes ovis, Sarcoptes rupicaprae (S. caprae), Sarcoptes equi,Sarcoptes suis, Psoroptes ovis, Psoroptes cuniculi, Psoroptes equi,Chorioptes bovis, Psoergates ovis, Pneumonyssoidic mange,Pneumonyssoides caninum, Acarapis woodi.

The active compounds according to the invention are also suitable forcontrolling arthropods, helminths and protozoae, which attack animals.

Animals include agricultural livestock such as, for example, cattle,sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits,chickens, turkeys, ducks, geese, cultured fish, honeybees.

Moreover, animals include domestic animals—also referred to as companionanimals—such as, for example, dogs, cats, cage birds, aquarium fish andwhat are known as experimental animals such as, for example, hamsters,guinea pigs, rats and mice.

By controlling these arthropods, helminths and/or protozoae, it isintended to reduce deaths and improve performance (in the case of meat,milk, wool, hides, eggs, honey and the like) and health of the hostanimal, so that more economical and simpler animal keeping is madepossible by the use of the active compounds according to the invention.

For example, it may be desirable to prevent or interrupt the uptake ofblood by the parasites from the hosts.

Also, controlling the parasites may help to prevent the transmittance ofinfectious agents.

The term “controlling” as used herein with regard to the veterinaryfield, means that the active compounds are effective in reducing theincidence of the respective parasite in an animal infected with suchparasites to innocuous levels.

More specifically, “controlling”, as used herein, means that the activecompound is effective in killing the respective parasite, inhibiting itsgrowth, or inhibiting its proliferation. Generally, when used for thetreatment of animals the active compounds according to the invention canbe applied directly.

Preferably they are applied as pharmaceutical compositions which maycontain pharmaceutically acceptable excipients and/or auxiliaries whichare known in the art.

In the veterinary field and in animal keeping, the active compounds areapplied (e.g. administered) in the known manner by enteraladministration in the form of, for example, tablets, capsules, drinks,drenches, granules, pastes, boluses, the feed-through method,suppositories; by parenteral administration, such as, for example, byinjections (intramuscular, subcutaneous, intravenous, intraperitonealand the like), implants, by nasal application, by dermal application inthe form of, for example, bathing or dipping, spraying, pouring-on andspotting-on, washing, dusting, and with the aid ofactive-compound-comprising shaped articles such as collars, ear tags,tail tags, limb bands, halters, marking devices and the like.

The active compounds may be formulated as shampoo or as suitableformulations usable in aerosols, unpressurized sprays, for example pumpsprays and atomizer sprays.

When used for livestock, poultry, domestic animals and the like, theactive compounds according to the invention can be applied asformulations (for example powders, wettable powders [“WP”], emulsions,emulsifiable concentrates [“EC”], flowables, homogeneous solutions, andsuspension concentrates [“SC”]) which comprise the active compounds inan amount of from 1 to 80 percent by weight, either directly or afterdilution (e.g. 100- to 10 000-fold dilution), or else as a chemicalbath.

When used in the veterinary field the active compounds according to theinvention may be used in combination with suitable synergists or otheractive compounds, such as for example, acaricides, insecticides,anthelmintics, anti-protozoal drugs.

In the present invention, a substance having an insecticidal actionagainst pests including all of these is referred to as an insecticide.

An active compound of the present invention can be prepared inconventional formulation forms, when used as an insecticide.

Examples of the formulation forms include solutions, emulsions, wettablepowders, water dispersible granules, suspensions, powders, foams,pastes, tablets, granules, aerosols, active compound-infiltrated naturaland synthetic materials, microcapsules, seed coating agents,formulations used with a combustion apparatus (for example, fumigationand smoking cartridges, cans, coils or the like as the combustionapparatus), ULV (cold mist, warm mist), and the like.

These formulations can be produced by methods that are known per se.

For example, a formulation can be produced by mixing the active compoundwith a developer, that is, a liquid diluent or carrier; a liquefied gasdiluent or carrier; a solid diluent or carrier, and optionally with asurfactant, that is, an emulsifier and/or dispersant and/or foamingagent.

In the case where water is used as the developer, for example, anorganic solvent can also be used as an auxiliary solvent.

Examples of the liquid diluent or carrier include aromatic hydrocarbons(for example, xylene, toluene, alkylnaphthalene and the like),chlorinated aromatic or chlorinated aliphatic hydrocarbons (for example,chlorobenzenes, ethylene chlorides, methylene chlorides), aliphatichydrocarbons (for example, cyclohexanes), paraffins (for example,mineral oil fractions), alcohols (for example, butanol, glycols andtheir ethers, esters and the like), ketones (for example, acetone,methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone and thelike), strongly polar solvents (for example, dimethylformamide,dimethylsulfoxide and the like), water and the like. The liquefied gasdiluent or carrier may be those which are gaseous at normal temperatureand normal pressure, for example, aerosol propellants such as butane,propane, nitrogen gas, carbon dioxide and halogenated hydrocarbons.Examples of the solid diluent include pulverized natural minerals (forexample, kaolin, clay, talc, chalk, quartz, attapulgite,montmorillonite, diatomaceous earth, and the like), pulverized syntheticminerals (for example, highly dispersed silicic acid, alumina, silicatesand the like), and the like. Examples of the solid carrier for granulesinclude pulverized and screened rocks (for example, calcite, marble,pumice, sepiolite, dolomite and the like), synthetic granules ofinorganic and organic powder, fine particles of organic materials (forexample, sawdust, coconut shells, maize cobs, tobacco stalk and thelike), and the like. Examples of the emulsifier and/or foaming agentinclude nonionic and anionic emulsifiers [for example, polyoxyethylenefatty acid esters, polyoxyethylene fatty acid alcohol ethers (forexample, alkylaryl polyglycol ether), alkylsulfonates, alkylsulfates,arylsulfonates and the like], albumin hydro lyzate, and the like.Examples of the dispersant include lignin sulfite waste liquor andmethylcellulose.

Fixing agents can also be used in the formulations (powders, granules,emulsions), and examples of the fixing agent includecarboxymethylcellulose, natural and synthetic polymers (for example, gumarabic, polyvinyl alcohol, polyvinyl acetate, and the like) and thelike. Colorants can also be used, and examples of the colorants includeinorganic pigments (for example, iron oxide, titanium oxide, PrussianBlue and the like), organic dyes such as alizarin dyes, azo dyes ormetal phthalocyanine dyes, and in addition, trace elements such as thesalts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.The formulations in general can contain the active ingredient in anamount ranging from 0.1 to 95 percent by weight, and preferably 0.5 to90 percent>by weight. The compound according to the present inventioncan also exist as an admixture with other active compounds, for example,insecticides, poisonous baits, bactericides, miticides, nematicides,fungicides, growth regulators, herbicides and the like, in the form oftheir commercially useful formulation forms and in the application formsprepared from those formulations.

The content of the compound according to the present invention in acommercially useful application form can be varied within a wide range.

The concentration of the active compound according to the presentinvention in actual usage can be, for example, in the range of 0.0000001to 100 percent by weight, and preferably 0.00001 to 1 percent by weight.

The compounds according to the present invention can be used throughconventional methods that are appropriate for the usage form.

The active compound of the present invention have, when used againsthygiene pests and pests associated with stored products, stabilityeffective against alkali on lime materials, and also shows excellentresidual effectiveness on wood and soil. The compounds of the inventionmay have favourable properties with respect to amount applied, residueformulation, selectivity, toxicity, production methodology, highactivity, wide spectrum of control, safety, control of resistantorganisms, e.g. pests that are resistant to organic phosphorus agentsand/or carbamate agents.

Further embodiments of the invention are described below.

The compounds of formula (I) can be used to combat and controlinfestations of insect pests such as Lepidoptera, Diptera, Hemiptera,Thysanoptera, Orthoptera, Dictyoptera, Coleoptera, Siphonaptera,Hymenoptera and Isoptera and also other invertebrate pests, for example,acarine, nematode and mollusc pests. Insects, acarines, nematodes andmolluscs are hereinafter collectively referred to as pests. The pestswhich may be combated and controlled by the use of the inventioncompounds include those pests associated with agriculture (which termincludes the growing of crops for food and fiber products), horticultureand animal husbandry, companion animals, forestry and the storage ofproducts of vegetable origin (such as fruit, grain and timber); thosepests associated with the damage of man-made structures and thetransmission of diseases of man and animals; and also nuisance pests(such as flies).

The compounds of the invention may be used for example on turf,ornamentals, such as flowers, shrubs, broad-leaved trees or evergreens,for example conifers, as well as for tree injection, pest management andthe like.

The compounds of the invention may be used to control animal housingpests including: Ants, Bedbugs (adult), Bees, Beetles, Boxelder Bugs,Carpenter Bees, Carpet Beetles, Centipedes, Cigarette, Beetles, CloverMites, Cockroaches, Confused Flour Beetle, Crickets, Earwigs, Firebrats,Fleas, Flies, Lesser Grain Borers, Millipedes, Mosquitoes, Red FlourBeetles, Rice Weevils, Saw-toothed Grain Beetles, Silverfish, Sowbugs,Spiders, Termites, Ticks, Wasps, Cockroaches, Crickets, Flies, LitterBeetles (such as Darkling, Hide, and Carrion), Mosquitoes, Pillbugs,Scorpions, Spiders, Spider Mites (Twospotted, Spruce), Ticks.

The compounds of the invention may be used to control ornamental pestsincluding: Ants (Including Imported fire ants), Armyworms, Azaleacaterpillars, Aphids, Bagworms, Black vine weevils (adult), Boxelderbugs, Budworms, California oakworms, Cankerworms, Cockroaches, Crickets,Cutworms, Eastern tent caterpillars, Elm leaf beetles, Europeansawflies, Fall webworms, Flea beetles, Forest tent caterpillars, Gypsymoth larvae, Japanese beetles (adults), June beetles (adults), Lacebugs, Leaf-feeding caterpillars, Leafhoppers, Leafminers (adults), Leafrollers, Leaf skeletonizers, Midges, Mosquitoes, Oleander moth larvae,Pillbugs, Pine sawflies, Pine shoot beetles, Pinetip moths, Plant bugs,Root weevils, Sawflies, Scale insects (crawlers), Spiders, Spittlebugs,Striped beetles, Striped oakworms, Thrips, Tip moths, Tussock mothlarvae, Wasps, Broadmites, Brown softscales, California redscales(crawlers), Clover mites, Mealybugs, Pineneedlescales (crawlers), Spidermites, Whiteflies

The compounds of the invention may be used to control turf pestsincluding: Ants (Including Imported fire ants, Armyworms, Centipedes,Crickets, Cutworms, Earwigs, Fleas (adult), Grasshoppers, Japanesebeetles (adult), Millipedes, Mites, Mosquitoes (adult), Pillbugs, Sodwebworms, Sow bugs, Ticks (including species which transmit Lymedisease), Bluegrass billbugs (adult), Black turfgrass ataenius (adult),Chiggers, Fleas (adult), Grubs (suppression), Hyperodes weevils (adult),Mole crickets (nymphs and young adults), Mole Crickets (mature adults),Chinch Bugs

Examples of pest species which may be controlled by the compounds offormula (I) include: Myzus persicae (aphid), Aphis gossypii (aphid),Aphis fabae (aphid), Lygus spp., (capsids), Dysdercus spp., (capsids),Nilaparvata lugens (planthopper), Nephotettixc incticeps (leafhopper),Nezara spp., (stinkbugs), Euschistus spp., (stinkbugs), Leptocorisaspp., (stinkbugs), Frankliniella occidentalis (thrip), Thrips spp.,(thrips), Leptinotarsa decemlineata (Colorado potato beetle), Anthonomusgrandis (boll weevil), Aonidiella spp., (scale insects), Trialeurodesspp., (white flies), Bemisia tabaci (white fly), Ostrinia nubilalis(European corn borer), Spodoptera littoralis (cotton leafworm),Heliothis virescens (tobacco budworm), Helicoverpa armigera (cottonbollworm), Helicoverpa zea (cotton bollworm), Sylepta derogata (cottonleaf roller), Pieris brassicae (white butterfly), Plutella xylostella(diamond back moth), Agrotis spp., (cutworms), Chilo suppressalis (ricestem borer), Locusta migratoria (locust), Chortiocetes terminifera(locust), Diabrotica spp., (rootworms), Panonychus ulmi (European redmite), Panonychus citri (citrus red mite), Tetranychus urticae(two-spotted spider mite), Tetranychus cinnabarinus (carmine spidermite), Phyllocoptruta oleivora (citrus rust mite), Polyphagotarsonemuslatus (broad mite), Brevipalpus spp., (flat mites), Boophilus microplus(cattle tick), Dermacentor variabilis (American dog tick),Ctenocephalides felis (cat flea), Liriomyza spp., (leafminer), Muscadomestica (housefly), Aedes aegypti (mosquito), Anopheles spp.,(mosquitoes), Culex spp., (mosquitoes), Lucillia spp., (blowflies),Blattella germanica (cockroach), Periplaneta americana (cockroach),Blatta orientalis (cockroach), termites of the Mastotermitidae (forexample Mastotermes spp.), the Kalotermitidae (for example Neotermesspp.), the Rhinotermitidae (for example Coptotermes formosanus,Reticulitermes flavipes, R. speratu, R. virginicus, R. hesperus, and R.santonensis) and the Termitidae (for example Globitermes sulfureus),Solenopsis geminata (fire ant), Monomorium pharaonis (pharaoh's ant),Damalinia spp., and Linognathus spp., (biting and sucking lice),Meloidogyne spp., (root knot nematodes), Globodera spp., and Heteroderaspp., (cyst nematodes), Pratylenchus spp., (lesion nematodes),Rhodopholus spp., (banana burrowing nematodes), Tylenchulus spp. (citrusnematodes), Haemonchus contortus (barber pole worm), Caenorhabditiselegans (vinegar eelworm), Trichostrongylus spp., (gastro intestinalnematodes) and Deroceras reticulatum (slug).

The compounds of the invention may be used for pest control on variousplants, including soybean (e.g. in some cases 10-70 g/ha), corn (e.g. insome cases 10-70 g/ha), sugarcane (e.g. in some cases 20-200 g/ha),alfalfa (e.g. in some cases 10-70 g/ha), brassicas (e.g. in some cases10-50 g/ha), oilseed rape (e.g. canola) (e.g. in some cases 20-70 g/ha),potatoes (including sweet potatoes) (e.g. in some cases 10-70 g/ha),cotton (e.g. in some cases 10-70 g/ha), rice (e.g. in some cases 10-70g/ha), coffee (e.g. in some cases 30-150 g/ha), citrus (e.g. in somecases 60-200 g/ha), almonds (e.g. in some cases 40-180 g/ha), fruitingvegetables (e.g. tomatoes, pepper, chili, eggplant, cucumber, squashetc.) (e.g. in some cases 10-80 g/ha), tea (e.g. in some cases 20-150g/ha), bulb vegetables (e.g. onion, leek etc.) (e.g. in some cases 30-90g/ha), grapes (e.g. in some cases 30-180 g/ha), pome fruit (e.g. apples,pears etc.) (e.g. in some cases 30-180 g/ha), and stone fruit (e.g.pears, plums etc.) (e.g. in some cases 30-180 g/ha).

The compounds of the invention may be used on soybean to control, forexample, Elasmopalpus lignosellus, Diloboderus abderus, Diabroticaspeciosa, Sternechus subsignatus, Formicidae, Agrotis ipsilon, Julusspp., Anticarsia gemmatalis, Megascelis spp., Procornitermes spp.,Gryllotalpidae, Nezara viridula, Piezodorus spp., Acrosternum spp.,Neomegalotomus spp., Cerotoma trifurcata, Popillia japonica, Edessaspp., Liogenys fuscus, Euchistus heros, stalk borer, Scaptocoriscastanea, phyllophaga spp., Pseudoplusia includens, Spodoptera spp.,Bemisia tabaci, Agriotes spp., The compounds of the invention arepreferably used on soybean to control Diloboderus abderus, Diabroticaspeciosa, Nezara viridula, Piezodorus spp., Acrosternum spp., Cerotomatrifurcata, Popillia japonica, Euchistus heros, phyllophaga spp.,Agriotes spp.

The compounds of the invention may be used on corn to control, forexample, Euchistus heros, Dichelops furcatus, Diloboderus abderus,Elasmopalpus lignosellus, Spodoptera frugiperda, Nezara viridula,Cerotoma trifurcata, Popillia japonica, Agrotis ypsilon, Diabroticaspeciosa, Heteroptera, Procornitermes ssp., Scaptocoris castanea,Formicidae, Julus ssp., Dalbulus maidis, Diabrotica virgifera, Mocislatipes, Bemisia tabaci, heliothis spp., Tetranychus spp., Thrips spp.,phyllophaga spp., scaptocoris spp., Liogenys fuscus, Spodoptera spp.,Ostrinia spp., Sesamia spp., Agriotes spp. The compounds of theinvention are preferably used on corn to control Euchistus heros,Dichelops furcatus, Diloboderus abderus, Nezara viridula, Cerotomatrifurcata, Popillia japonica, Diabrotica speciosa, Diabroticavirgifera, Tetranychus spp., Thrips spp., Phyllophaga spp., Scaptocorisspp., Agriotes spp.

The compounds of the invention may be used on sugar cane to control, forexample, Sphenophorus spp., termites, Mahanarva spp. The compounds ofthe invention are preferably used on sugar cane to control termites,Mahanarva spp.

The compounds of the invention may be used on alfalfa to control, forexample, Hypera brunneipennis, Hypera postica, Colias eurytheme, Collopsspp., Empoasca solana, Epitrix, Geocoris spp., Lygus hesperus, Lyguslineolaris, Spissistilus spp., Spodoptera spp., Trichoplusia ni. Thecompounds of the invention are preferably used on alfalfa to controlHypera brunneipennis, Hypera postica, Empoasca solana, Epitrix, Lygushesperus, Lygus lineolaris, Trichoplusia ni.

The compounds of the invention may be used on brassicas to control, forexample, Plutella xylostella, Pieris spp., Mamestra spp., Plusia spp.,Trichoplusia ni, Phyllotreta spp., Spodoptera spp., Empoasca solana,Thrips spp., Spodoptera spp., Delia spp. The compounds of the inventionare preferably used on brassicas to control Plutella xylostella Pierisspp., Plusia spp., Trichoplusia ni, Phyllotreta spp., Thrips spp.

The compounds of the invention may be used on oil seed rape, e.g.canola, to control, for example, Meligethes spp., Ceutorhynchus napi,Psylloides spp.

The compounds of the invention may be used on potatoes, including sweetpotatoes, to control, for example, Empoasca spp., Leptinotarsa spp.,Diabrotica speciosa, Phthorimaea spp., Paratrioza spp., Maladeramatrida, Agriotes spp. The compounds of the invention are preferablyused on potatoes, including sweet potatoes, to control Empoasca spp.,Leptinotarsa spp., Diabrotica speciosa, Phthorimaea spp., Paratriozaspp., Agriotes spp.

The compounds of the invention may be used on cotton to control, forexample, Anthonomus grandis, Pectinophora spp., heliothis spp.,Spodoptera spp., Tetranychus spp., Empoasca spp., Thrips spp., Bemisiatabaci, Lygus spp., phyllophaga spp., Scaptocoris spp. The compounds ofthe invention are preferably used on cotton to control Anthonomusgrandis, Tetranychus spp., Empoasca spp., Thrips spp., Lygus spp.,phyllophaga spp., Scaptocoris spp.

The compounds of the invention may be used on rice to control, forexample, Leptocorisa spp., Cnaphalocrosis spp., Chilo spp., Scirpophagaspp., Lissorhoptrus spp., Oebalus pugnax. The compounds of the inventionare preferably used on rice to control Leptocorisa spp., Lissorhoptrusspp., Oebalus pugnax.

The compounds of the invention may be used on coffee to control, forexample, Hypothenemus Hampei, Perileucoptera Coffeella, Tetranychusspp., The compounds of the invention are preferably used on coffee tocontrol Hypothenemus Hampei, Perileucoptera Coffeella.

The compounds of the invention may be used on citrus to control, forexample, Panonychus citri, Phyllocoptruta oleivora, Brevipalpus spp.,Diaphorina citri, Scirtothrips spp., Thrips spp., Unaspis spp.,Ceratitis capitata, Phyllocnistis spp. The compounds of the inventionare preferably used on citrus to control Panonychus citri,Phyllocoptruta oleivora, Brevipalpus spp, Diaphorina citri, Scirtothripsspp., Thrips spp., Phyllocnistis spp.

The compounds of the invention may be used on almonds to control, forexample, Amyelois transitella, Tetranychus spp.

The compounds of the invention may be used on fruiting vegetable,including tomatoes, pepper, chili, eggplant, cucumber, squash etc, tocontrol Thrips spp, Tetranychus spp., Polyphagotarsonemus spp., Aculopsspp., Empoasca spp., Spodoptera spp., heliothis spp., Tuta absoluta,Liriomyza spp., Bemisia tabaci, Trialeurodes spp., Paratrioza spp.,Frankliniella occidentalis, Frankliniella spp., Anthonomus spp.,Phyllotreta spp., Amrasca spp., Epilachna spp., Halyomorpha spp.,Scirtothrips spp., Leucinodes spp., Neoleucinodes spp. The compounds ofthe invention are preferably used on fruiting vegetable, includingtomatoes, pepper, chili, eggplant, cucumber, squash etc, to control, forexample, Thrips spp., Tetranychus spp., Polyphagotarsonemus spp.,Aculops spp., Empoasca spp., Spodoptera spp., heliothis spp., Tutaabsoluta, Liriomyza spp., Paratrioza spp., Frankliniella occidentalis,Frankliniella spp., Amrasca spp., Scirtothrips spp., Leucinodes spp.,Neoleucinodes spp.

The compounds of the invention may be used on tea to control, forexample, Pseudaulacaspis spp., Empoasca spp., Scirtothrips spp.,Caloptilia theivora. The compounds of the invention are preferably usedon tea to control Empoasca spp., Scirtothrips spp.

The compounds of the invention may be used on bulb vegetables, includingonion, leek etc to control, for example, Thrips spp., Spodoptera spp.,heliothis spp. The compounds of the invention are preferably used onbulb vegetables, including onion, leek etc to control Thrips spp.

The compounds of the invention may be used on grapes to control, forexample, Empoasca spp., Lobesia spp., Frankliniella spp., Thrips spp.,Tetranychus spp., Rhipiphorothrips Cruentatus, EotetranychusWillamettei, Erythroneura Elegantula, Scaphoides spp. The compounds ofthe invention are preferably used on grapes to control Frankliniellaspp., Thrips spp., Tetranychus spp., Rhipiphorothrips Cruentatus,Scaphoides spp.

The compounds of the invention may be used on pome fruit, includingapples, pears etc, to control, for example, Cacopsylla spp., Psyllaspp., Panonychus ulmi, Cydia pomonella. The compounds of the inventionare preferably used on pome fruit, including apples, pears etc, tocontrol Cacopsylla spp., Psylla spp., Panonychus ulmi.

The compounds of the invention may be used on stone fruit to control,for example, Grapholita molesta, Scirtothrips spp., Thrips spp.,Frankliniella spp., Tetranychus spp. The compounds of the invention arepreferably used on stone fruit to control Scirtothrips spp., Thripsspp., Frankliniella spp., Tetranychus spp. The invention thereforeprovides a method of combating and/or controlling an animal pest, e.g.an invertebrate animal pest, which comprises applying to the pest, to alocus of the pest, or to a plant susceptible to attack by the pest apesticidally effective amount of a compound of formula (I). Inparticular, the invention provides a method of combating and/orcontrolling insects, acarines, nematodes or molluscs which comprisesapplying an insecticidally, acaricidally, nematicidally ormolluscicidally effective amount of a compound of formula (I), or acomposition containing a compound of formula (I), to a pest, a locus ofpest, preferably a plant, or to a plant susceptible to attack by a pest,The compounds of formula (I) are preferably used against insects,acarines or nematodes.

The term “plant” as used herein includes seedlings, bushes and trees.Crops are to be understood as also including those crops which have beenrendered tolerant to herbicides or classes of herbicides (e.g. ALS-,GS-, EPSPS-, PPO- and HPPD-inhibitors) by conventional methods ofbreeding or by genetic engineering. An example of a crop that has beenrendered tolerant to imidazolinones, e.g. imazamox, by conventionalmethods of breeding is Clearfield® summer rape (canola). Examples ofcrops that have been rendered tolerant to herbicides by geneticengineering methods include e.g. glyphosate- and glufosinate-resistantmaize varieties commercially available under the trade namesRoundupReady® and LibertyLink®.

Crops are also to be understood as being those which have been renderedresistant to harmful insects by genetic engineering methods, for exampleBt maize (resistant to European corn borer), Bt cotton (resistant tocotton boll weevil) and also Bt potatoes (resistant to Colorado beetle).Examples of Bt maize are the Bt 176 maize hybrids of NK® (SyngentaSeeds). Examples of transgenic plants comprising one or more genes thatcode for an insecticidal resistance and express one or more toxins areKnockOut® (maize), Yield Gard® (maize), NuCOTIN33B® (cotton), Bollgard®(cotton), NewLeaf® (potatoes), NatureGard® and Protexcta®. Plant cropsor seed material thereof can be both resistant to herbicides and, at thesame time, resistant to insect feeding (“stacked” transgenic events).For example, seed can have the ability to express an insecticidal Cry3protein while at the same time being tolerant to glyphosate.

Crops are also to be understood as being those which are obtained byconventional methods of breeding or genetic engineering and containso-called output traits (e.g. improved storage stability, highernutritional value and improved flavor).

In order to apply a compound of formula (I) as an insecticide,acaricide, nematicide or molluscicide to a pest, a locus of pest, or toa plant susceptible to attack by a pest, a compound of formula (I) isusually formulated into a composition which includes, in addition to thecompound of formula (I), a suitable inert diluent or carrier and,optionally, a surface active agent (SFA). SFAs are chemicals which areable to modify the properties of an interface (for example,liquid/solid, liquid/air or liquid/liquid interfaces) by lowering theinterfacial tension and thereby leading to changes in other properties(for example dispersion, emulsification and wetting). It is preferredthat all compositions (both solid and liquid formulations) comprise, byweight, 0.0001 to 95%, more preferably 1 to 85%, for example 5 to 60%,of a compound of formula (I). The composition is generally used for thecontrol of pests such that a compound of formula (I) is applied at arate of from 0.1 g to 10 kg per hectare, preferably from 1 g to 6 kg perhectare, more preferably from 1 g to 1 kg per hectare.

When used in a seed dressing, a compound of formula (I) is generallyused at a rate of 0.0001 g to 10 g (for example 0.001 g or 0.05 g),preferably 0.005 g to 10 g, more preferably 0.005 g to 4 g, per kilogramof seed.

In another aspect the present invention provides a compositioncomprising a pesticidally effective amount of a compound of formula (I),in particular an insecticidal, acaricidal, nematicidal or molluscicidalcomposition comprising an insecticidally, acaricidally, nematicidally ormolluscicidally effective amount of a compound of formula (I) and asuitable carrier or diluent therefor. The composition is preferably aninsecticidal, acaricidal, nematicidal or molluscicidal composition.

The compositions can be chosen from a number of formulation types,including dustable powders (DP), soluble powders (SP), water solublegranules (SG), water dispersible granules (WG), wettable powders (WP),granules (GR) (slow or fast release), soluble concentrates (SL), oilmiscible liquids (OL), ultra low volume liquids (UL), emulsifiableconcentrates (EC), dispersible concentrates (DC), emulsions (both oil inwater (EW) and water in oil (EO)), micro-emulsions (ME), suspensionconcentrates (SC), aerosols, fogging/smoke formulations, capsulesuspensions (CS) and seed treatment formulations. The formulation typechosen in any instance will depend upon the particular purpose envisagedand the physical, chemical and biological properties of the compound offormula (I).

Dustable powders (DP) may be prepared by mixing a compound of formula(I) with one or more solid diluents (for example natural clays, kaolin,pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk,diatomaceous earths, calcium phosphates, calcium and magnesiumcarbonates, sulfur, lime, flours, talc and other organic and inorganicsolid carriers) and mechanically grinding the mixture to a fine powder.

Soluble powders (SP) may be prepared by mixing a compound of formula (I)with one or more water-soluble inorganic salts (such as sodiumbicarbonate, sodium carbonate or magnesium sulfate) or one or morewater-soluble organic solids (such as a polysaccharide) and, optionally,one or more wetting agents, one or more dispersing agents or a mixtureof said agents to improve water dispersibility/solubility. The mixtureis then ground to a fine powder. Similar compositions may also begranulated to form water soluble granules (SG).

Wettable powders (WP) may be prepared by mixing a compound of formula(I) with one or more solid diluents or carriers, one or more wettingagents and, preferably, one or more dispersing agents and, optionally,one or more suspending agents to facilitate the dispersion in liquids.The mixture is then ground to a fine powder. Similar compositions mayalso be granulated to form water dispersible granules (WG).

Granules (GR) may be formed either by granulating a mixture of acompound of formula (I) and one or more powdered solid diluents orcarriers, or from pre-formed blank granules by absorbing a compound offormula (I) (or a solution thereof, in a suitable agent) in a porousgranular material (such as pumice, attapulgite clays, fuller's earth,kieselguhr, diatomaceous earths or ground corn cobs) or by adsorbing acompound of formula (I) (or a solution thereof, in a suitable agent) onto a hard core material (such as sands, silicates, mineral carbonates,sulfates or phosphates) and drying if necessary. Agents which arecommonly used to aid absorption or adsorption include solvents (such asaliphatic and aromatic petroleum solvents, alcohols, ethers, ketones andesters) and sticking agents (such as polyvinyl acetates, polyvinylalcohols, dextrins, sugars and vegetable oils). One or more otheradditives may also be included in granules (for example an emulsifyingagent, wetting agent or dispersing agent).

Dispersible Concentrates (DC) may be prepared by dissolving a compoundof formula (I) in water or an organic solvent, such as a ketone, alcoholor glycol ether. These solutions may contain a surface active agent (forexample to improve water dilution or prevent crystallization in a spraytank).

Emulsifiable concentrates (EC) or oil-in-water emulsions (EW) may beprepared by dissolving a compound of formula (I) in an organic solvent(optionally containing one or more wetting agents, one or moreemulsifying agents or a mixture of said agents). Suitable organicsolvents for use in ECs include aromatic hydrocarbons (such asalkylbenzenes or alkylnaphthalenes, exemplified by SOLVESSO 100,SOLVESSO 150 and SOLVESSO 200; SOLVESSO is a Registered Trade Mark),ketones (such as cyclohexanone or methylcyclohexanone) and alcohols(such as benzyl alcohol, furfuryl alcohol or butanol),N-alkypyrrolidones (such as N-methylpyrrolidone or N-octylpyrrolidone),dimethyl amides of fatty acids (such as C₈-C₁₀ fatty acid dimethylamide)and chlorinated hydrocarbons. An EC product may spontaneously emulsifyon addition to water, to produce an emulsion with sufficient stabilityto allow spray application through appropriate equipment. Preparation ofan EW involves obtaining a compound of formula (I) either as a liquid(if it is not a liquid at room temperature, it may be melted at areasonable temperature, typically below 70° C.) or in solution (bydissolving it in an appropriate solvent) and then emulsifying theresultant liquid or solution into water containing one or more SFAs,under high shear, to produce an emulsion. Suitable solvents for use inEWs include vegetable oils, chlorinated hydrocarbons (such aschlorobenzenes), aromatic solvents (such as alkylbenzenes oralkylnaphthalenes) and other appropriate organic solvents which have alow solubility in water.

Microemulsions (ME) may be prepared by mixing water with a blend of oneor more solvents with one or more SFAs, to produce spontaneously athermodynamically stable isotropic liquid formulation. A compound offormula (I) is present initially in either the water or the solvent/SFAblend. Suitable solvents for use in MEs include those hereinbeforedescribed for use in ECs or in EWs. An ME may be either an oil-in-wateror a water-in-oil system (which system is present may be determined byconductivity measurements) and may be suitable for mixing water-solubleand oil-soluble pesticides in the same formulation. An ME is suitablefor dilution into water, either remaining as a microemulsion or forminga conventional oil-in-water emulsion.

Suspension concentrates (SC) may comprise aqueous or non-aqueoussuspensions of finely divided insoluble solid particles of a compound offormula (I). SCs may be prepared by ball or bead milling the solidcompound of formula (I) in a suitable medium, optionally with one ormore dispersing agents, to produce a fine particle suspension of thecompound. One or more wetting agents may be included in the compositionand a suspending agent may be included to reduce the rate at which theparticles settle. Alternatively, a compound of formula (I) may be drymilled and added to water, containing agents hereinbefore described, toproduce the desired end product.

Aerosol formulations comprise a compound of formula (I) and a suitablepropellant (for example n-butane). A compound of formula (I) may also bedissolved or dispersed in a suitable medium (for example water or awater miscible liquid, such as n-propanol) to provide compositions foruse in non-pressurized, hand-actuated spray pumps.

A compound of formula (I) may be mixed in the dry state with apyrotechnic mixture to form a composition suitable for generating, in anenclosed space, a smoke containing the compound.

Capsule suspensions (CS) may be prepared in a manner similar to thepreparation of EW formulations but with an additional polymerizationstage such that an aqueous dispersion of oil droplets is obtained, inwhich each oil droplet is encapsulated by a polymeric shell and containsa compound of formula (I) and, optionally, a carrier or diluenttherefor. The polymeric shell may be produced by either an interfacialpolycondensation reaction or by a coacervation procedure. Thecompositions may provide for controlled release of the compound offormula (I) and they may be used for seed treatment. A compound offormula (I) may also be formulated in a biodegradable polymeric matrixto provide a slow, controlled release of the compound.

A composition may include one or more additives to improve thebiological performance of the composition (for example by improvingwetting, retention or distribution on surfaces; resistance to rain ontreated surfaces; or uptake or mobility of a compound of formula (I)).Such additives include surface active agents, spray additives based onoils, for example certain mineral oils or natural plant oils (such assoy bean and rape seed oil), and blends of these with otherbio-enhancing adjuvants (ingredients which may aid or modify the actionof a compound of formula (I)).

A compound of formula (I) may also be formulated for use as a seedtreatment, for example as a powder composition, including a powder fordry seed treatment (DS), a water soluble powder (SS) or a waterdispersible powder for slurry treatment (WS), or as a liquidcomposition, including a flowable concentrate (FS), a solution (LS) or acapsule suspension (CS). The preparations of DS, SS, WS, FS and LScompositions are very similar to those of, respectively, DP, SP, WP, SCand DC compositions described above. Compositions for treating seed mayinclude an agent for assisting the adhesion of the composition to theseed (for example a mineral oil or a film-forming barrier).

Wetting agents, dispersing agents and emulsifying agents may be surfaceSFAs of the cationic, anionic, amphoteric or non-ionic type.

Suitable SFAs of the cationic type include quaternary ammonium compounds(for example cetyltrimethyl ammonium bromide), imidazolines and aminesalts.

Suitable anionic SFAs include alkali metals salts of fatty acids, saltsof aliphatic monoesters of sulfuric acid (for example sodium laurylsulfate), salts of sulfonated aromatic compounds (for example sodiumdodecylbenzenesulfonate, calcium dodecylbenzenesulfonate,butylnaphthalene sulfonate and mixtures of sodium di-isopropyl- andtri-isopropyl-naphthalene sulfonates), ether sulfates, alcohol ethersulfates (for example sodium laureth-3-sulfate), ether carboxylates (forexample sodium laureth-3-carboxylate), phosphate esters (products fromthe reaction between one or more fatty alcohols and phosphoric acid(predominately mono-esters) or phosphorus pentoxide (predominatelydi-esters), for example the reaction between lauryl alcohol andtetraphosphoric acid; additionally these products may be ethoxylated),sulfosuccinamates, paraffin or olefine sulfonates, taurates andlignosulfonates.

Suitable SFAs of the amphoteric type include betaines, propionates andglycinates.

Suitable SFAs of the non-ionic type include condensation products ofalkylene oxides, such as ethylene oxide, propylene oxide, butylene oxideor mixtures thereof, with fatty alcohols (such as oleyl alcohol or cetylalcohol) or with alkylphenols (such as octylphenol, nonylphenol oroctylcresol); partial esters derived from long chain fatty acids orhexitol anhydrides; condensation products of said partial esters withethylene oxide; block polymers (comprising ethylene oxide and propyleneoxide); alkanolamides; simple esters (for example fatty acidpolyethylene glycol esters); amine oxides (for example lauryl dimethylamine oxide); and lecithins

Suitable suspending agents include hydrophilic colloids (such aspolysaccharides, polyvinylpyrrolidone or sodium carboxymethylcellulose)and swelling clays (such as bentonite or attapulgite).

A compound of formula (I) may be applied by any of the known means ofapplying pesticidal compounds. For example, it may be applied,formulated or unformulated, to the pests or to a locus of the pests(such as a habitat of the pests, or a growing plant liable toinfestation by the pests) or to any part of the plant, including thefoliage, stems, branches or roots, to the seed before it is planted orto other media in which plants are growing or are to be planted (such assoil surrounding the roots, the soil generally, paddy water orhydroponic culture systems), directly or it may be sprayed on, dustedon, applied by dipping, applied as a cream or paste formulation, appliedas a vapor or applied through distribution or incorporation of acomposition (such as a granular composition or a composition packed in awater-soluble bag) in soil or an aqueous environment.

A compound of formula (I) may also be injected into plants or sprayedonto vegetation using electrodynamic spraying techniques or other lowvolume methods, or applied by land or aerial irrigation systems.

Compositions for use as aqueous preparations (aqueous solutions ordispersions) are generally supplied in the form of a concentratecontaining a high proportion of the active ingredient, the concentratebeing added to water before use. These concentrates, which may includeDCs, SCs, ECs, EWs, MEs, SGs, SPs, WPs, WGs and CSs, are often requiredto withstand storage for prolonged periods and, after such storage, tobe capable of addition to water to form aqueous preparations whichremain homogeneous for a sufficient time to enable them to be applied byconventional spray equipment. Such aqueous preparations may containvarying amounts of a compound of formula (I) (for example 0.0001 to 10%,by weight) depending upon the purpose for which they are to be used.

A compound of formula (I) may be used in mixtures with fertilizers (forexample nitrogen-, potassium- or phosphorus-containing fertilizers).Suitable formulation types include granules of fertilizer. The mixturespreferably contain up to 25% by weight of the compound of formula (I).

The invention therefore also provides a fertilizer compositioncomprising a fertilizer and a compound of formula (I).

The compositions of this invention may contain other compounds havingbiological activity, for example micronutrients or compounds havingfungicidal activity or which possess plant growth regulating,herbicidal, insecticidal, nematicidal or acaricidal activity.

The compound of formula (I) may be the sole active ingredient of thecomposition or it may be admixed with one or more additional activeingredients such as a pesticide, e.g. a insecticide, fungicide orherbicide, or a synergist or plant growth regulator where appropriate.An additional active ingredient may provide a composition having abroader spectrum of activity or increased persistence at a locus;synergize the activity or complement the activity (for example byincreasing the speed of effect or overcoming repellency) of the compoundof formula (I); or help to overcome or prevent the development ofresistance to individual components. The particular additional activeingredient will depend upon the intended utility of the composition.

The compounds of the invention are also useful in the field of animalhealth, e.g. they may be used against parasitic invertebrate pests, morepreferably against parasitic invertebrate pests in or on an animal.Examples of pests include nematodes, trematodes, cestodes, flies, mites,tricks, lice, fleas, true bugs and maggots. The animal may be anon-human animal, e.g. an animal associated with agriculture, e.g. acow, a pig, a sheep, a goat, a horse, or a donkey, or a companionanimal, e.g. a dog or a cat.

In a further aspect the invention provides a compound of the inventionfor use in a method of therapeutic treatment.

In a further aspect the invention relates to a method of controllingparasitic invertebrate pests in or on an animal comprising administeringa pesticidally effective amount of a compound of the invention. Theadministration may be for example oral administration, parenteraladministration or external administration, e.g. to the surface of theanimal body. In a further aspect the invention relates to a compound ofthe invention for controlling parasitic invertebrate pests in or on ananimal. In a further aspect the invention relates to use of a compoundof the invention in the manufacture of a medicament for controllingparasitic invertebrate pests in or on an animal

In a further aspect, the invention relates to a method of controllingparasitic invertebrate pests comprising administering a pesticidallyeffective amount of a compound of the invention to the environment inwhich an animal resides.

In a further aspect the invention relates to a method of protecting ananimal from a parasitic invertebrate pest comprising administering tothe animal a pesticidally effective amount of a compound of theinvention. In a further aspect the invention relates to a compound ofthe invention for use in protecting an animal from a parasiticinvertebrate pest. In a further aspect the invention relates to use of acompound of the invention in the manufacture of a medicament forprotecting an animal from a parasitic invertebrate pest.

In a further aspect the invention provides a method of treating ananimal suffering from a parasitic invertebrate pest comprisingadministering to the animal a pesticidally effective amount of acompound of the invention. In a further aspect the invention relates toa compound of the invention for use in treating an animal suffering froma parasitic invertebrate pest. In a further aspect the invention relatesto use of a compound of the invention in the manufacture of a medicamentfor treating an animal suffering from a parasitic invertebrate pest.

In a further aspect, the invention provides a pharmaceutical compositioncomprising a compound of the invention and a pharmaceutically suitableexcipient.

The compounds of the invention may be used alone or in combination withone or more other biologically active ingredients.

In one aspect the invention provides a combination product comprising apesticidally effective amount of a component A and a pesticidallyeffective amount of component B wherein component A is a compound of theinvention and component B is a compound as described below.

The compounds of the invention may be used in combination withanthelmintic agents. Such anthelmintic agents include, compoundsselected from the macrocyclic lactone class of compounds such asivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin,selamectin, moxidectin, nemadectin and milbemycin derivatives asdescribed in EP-357460, EP-444964 and EP-594291. Additional anthelminticagents include semisynthetic and biosynthetic avermectin/milbemycinderivatives such as those described in U.S. Pat. No. 5,015,630,WO-9415944 and WO-9522552. Additional anthelmintic agents include thebenzimidazoles such as albendazole, cambendazole, fenbendazole,flubendazole, mebendazole, oxfendazole, oxibendazole, parbendazole, andother members of the class. Additional anthelmintic agents includeimidazothiazoles and tetrahydropyrimidines such as tetramisole,levamisole, pyrantel pamoate, oxantel or morantel. Additionalanthelmintic agents include flukicides, such as triclabendazole andclorsulon and the cestocides, such as praziquantel and epsiprantel.

The compounds of the invention may be used in combination withderivatives and analogues of the paraherquamide/marcfortine class ofanthelmintic agents, as well as the antiparasitic oxazolines such asthose disclosed in U.S. Pat. No. 5,478,855, U.S. Pat. No. 4,639,771 andDE-19520936.

The compounds of the invention may be used in combination withderivatives and analogues of the general class of dioxomorpholineantiparasitic agents as described in WO-9615121 and also withanthelmintic active cyclic depsipeptides such as those described inWO-9611945, WO-9319053, WO-9325543, EP-626375, EP-382173, WO-9419334,EP-382173, and EP-503538.

The compounds of the invention may be used in combination with otherectoparasiticides; for example, fipronil; pyrethroids; organophosphates;insect growth regulators such as lufenuron; ecdysone agonists such astebufenozide and the like; neonicotinoids such as imidacloprid and thelike.

The compounds of the invention may be used in combination with terpenealkaloids, for example those described in International PatentApplication Publication Numbers WO95/19363 or WO04/72086, particularlythe compounds disclosed therein.

Other examples of such biologically active compounds that the compoundsof the invention may be used in combination with include but are notrestricted to the following:

Organophosphates: acephate, azamethiphos, azinphos-ethyl,azinphos-methyl, bromophos, bromophos-ethyl, cadusafos, chlorethoxyphos,chlorpyrifos, chlorfenvinphos, chlormephos, demeton, demeton-S-methyl,demeton-S-methyl sulphone, dialifos, diazinon, dichlorvos, dicrotophos,dimethoate, disulfoton, ethion, ethoprophos, etrimfos, famphur,fenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazofos,fonofos, formothion, fosthiazate, heptenophos, isazophos, isothioate,isoxathion, malathion, methacriphos, methamidophos, methidathion,methyl-parathion, mevinphos, monocrotophos, naled, omethoate,oxydemeton-methyl, paraoxon, parathion, parathion-methyl, phenthoate,phosalone, phosfolan, phosphocarb, phosmet, phosphamidon, phorate,phoxim, pirimiphos, pirimiphos-methyl, profenofos, propaphos,proetamphos, prothiofos, pyraclofos, pyridapenthion, quinalphos,sulprophos, temephos, terbufos, tebupirimfos, tetrachlorvinphos,thimeton, triazophos, trichlorfon, vamidothion.

Carbamates: alanycarb, aldicarb, 2-sec-butylphenyl methylcarbamate,benfuracarb, carbaryl, carbofuran, carbosulfan, cloethocarb,ethiofencarb, fenoxycarb, fenthiocarb, furathiocarb, HCN-801,isoprocarb, indoxacarb, methiocarb, methomyl,5-methyl-m-cumenylbutyryl(methyl)carbamate, oxamyl, pirimicarb,propoxur, thiodicarb, thiofanox, triazamate, UC-51717.

Pyrethroids: acrinathin, allethrin, alphametrin, 5-benzyl-3-furylmethyl(E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate,bifenthrin, beta-cyfluthrin, cyfluthrin, a-cypermethrin,beta-cypermethrin, bioallethrin, bioallethrin((S)-cyclopentylisomer),bioresmethrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin,cythithrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate,ethofenprox, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate,flumethrin, fluvalinate (D isomer), imiprothrin, cyhalothrin,lambda-cyhalothrin, permethrin, phenothrin, prallethrin, pyrethrins(natural products), resmethrin, tetramethrin, transfluthrin,theta-cypermethrin, silafluofen, t-fluvalinate, tefluthrin,tralomethrin, Zeta-cypermethrin.

Arthropod growth regulators: a) chitin synthesis inhibitors:benzoylureas: chlorfluazuron, diflubenzuron, fluazuron, flucycloxuron,flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron,triflumuron, buprofezin, diofenolan, hexythiazox, etoxazole,chlorfentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide,tebufenozide; c) juvenoids: pyriproxyfen, methoprene (includingS-methoprene), fenoxycarb; d) lipid biosynthesis inhibitors:spirodiclofen.

Other antiparasitics: acequinocyl, amitraz, AKD-1022, ANS-118,azadirachtin, Bacillus thuringiensis, bensultap, bifenazate, binapacryl,bromopropylate, BTG-504, BTG-505, camphechlor, cartap, chlorobenzilate,chlordimeform, chlorfenapyr, chromafenozide, clothianidine, cyromazine,diacloden, diafenthiuron, DBI-3204, dinactin,dihydroxymethyldihydroxypyrrolidine, dinobuton, dinocap, endosulfan,ethiprole, ethofenprox, fenazaquin, flumite, MTI-800, fenpyroximate,fluacrypyrim, flubenzimine, flubrocythrinate, flufenzine, flufenprox,fluproxyfen, halo fenprox, hydramethylnon, IKI-220, kanemite, NC-196,neem guard, nidinorterfuran, nitenpyram, SD-35651, WL-108477, pirydaryl,propargite, protrifenbute, pymethrozine, pyridaben, pyrimidifen,NC-1111, R-195, RH-0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601,silafluofen, silomadine, spinosad, tebufenpyrad, tetradifon,tetranactin, thiacloprid, thiocyclam, thiamethoxam, tolfenpyrad,triazamate, triethoxyspinosyn, trinactin, verbutin, vertalec, YI-5301.

Fungicides: acibenzolar, aldimorph, ampropylfos, andoprim, azaconazole,azoxystrobin, benalaxyl, benomyl, bialaphos, blasticidin-S, Bordeauxmixture, bromuconazole, bupirimate, carpropamid, captafol, captan,carbendazim, chlorfenazole, chloroneb, chloropicrin, chlorothalonil,chlozolinate, copper oxychloride, copper salts, cyflufenamid, cymoxanil,cyproconazole, cyprodinil, cyprofuram, RH-7281, diclocymet,diclobutrazole, diclomezine, dicloran, difenoconazole, RP-407213,dimethomorph, domoxystrobin, diniconazole, diniconazole-M, dodine,edifenphos, epoxiconazole, famoxadone, fenamidone, fenarimol,fenbuconazole, fencaramid, fenpiclonil, fenpropidin, fenpropimorph,fentin acetate, fluazinam, fludioxonil, flumetover, flumorf/flumorlin,fentin hydroxide, fluoxastrobin, fluquinconazole, flusilazole,flutolanil, flutriafol, folpet, fosetyl-aluminium, furalaxyl,furametapyr, hexaconazole, ipconazole, iprobenfos, iprodione,isoprothiolane, kasugamycin, krsoxim-methyl, mancozeb, maneb, mefenoxam,mepronil, metalaxyl, metconazole, metominostrobin/fenominostrobin,metrafenone, myclobutanil, neo-asozin, nicobifen, orysastrobin,oxadixyl, penconazole, pencycuron, probenazole, prochloraz, propamocarb,propioconazole, proquinazid, prothioconazole, pyrifenox, pyraclostrobin,pyrimethanil, pyroquilon, quinoxyfen, spiroxamine, sulfur, tebuconazole,tetrconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram,tiadinil, triadimefon, triadimenol, tricyclazole, trifloxystrobin,triticonazole, validamycin, vinclozin.

Biological agents: Bacillus thuringiensis ssp aizawai, kurstaki,Bacillus thuringiensis delta endotoxin, baculovirus, entomopathogenicbacteria, virus and fungi.

Bactericides: chlortetracycline, oxytetracycline, streptomycin.

Other biological agents: enrofloxacin, febantel, penethamate, moloxicam,cefalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin,benazepril, pyriprole, cefquinome, florfenicol, buserelin, cefovecin,tulathromycin, ceftiour, carprofen, metaflumizone, praziquarantel,triclabendazole.

When used in combination with other active ingredients, the compounds ofthe invention are preferably used in combination with the following(where “Tx” means a compound of formula (I), and in particular one thecompound of the formula (I) or one specific compound selected from theTable A1 to A12 and Table B, which may result in a synergisticcombination with the given active ingredient): imidacloprid+Tx,enrofloxacin+Tx, praziquantel+Tx, pyrantel embonate+Tx, febantel+Tx,penethamate+Tx, moloxicam+Tx, cefalexin+Tx, kanamycin+Tx, pimobendan+Tx,clenbuterol+Tx, fipronil+Tx, ivermectin+Tx, omeprazole+Tx, tiamulin+Tx,benazepril+Tx, milbemycin+Tx, cyromazine+Tx, thiamethoxam+Tx,pyriprole+Tx, deltamethrin+Tx, cefquinome+Tx, florfenicol+Tx,buserelin+Tx, cefovecin+Tx, tulathromycin+Tx, ceftiour+Tx,selamectin+Tx, carprofen+Tx, metaflumizone+Tx, moxidectin+Tx, methoprene(including S-methoprene)+Tx, clorsulon+Tx, pyrantel+Tx, amitraz+Tx,triclabendazole+Tx, avermectin+Tx, abamectin+Tx, emamectin+Tx,eprinomectin+Tx, doramectin+Tx, selamectin+Tx, nemadectin+Tx,albendazole+Tx, cambendazole+Tx, fenbendazole+Tx, flubendazole+Tx,mebendazole+Tx, oxfendazole+Tx, oxibendazole+Tx, parbendazole+Tx,tetramisole+Tx, levamisole+Tx, pyrantel pamoate+Tx, oxantel+Tx,morantel+Tx, triclabendazole+Tx, epsiprantel+Tx, flpronil+Tx,lufenuron+Tx, ecdysone+Tx or tebufenozide+Tx; more preferably,enrofloxacin+Tx, praziquantel+Tx, pyrantel embonate+Tx, febantel+Tx,penethamate+Tx, moloxicam+Tx, cefalexin+Tx, kanamycin+Tx, pimobendan+Tx,clenbuterol+Tx, omeprazole+Tx, tiamulin+Tx, benazepril+Tx, pyriprole+Tx,cefquinome+Tx, florfenicol+Tx, buserelin+Tx, cefovecin+Tx,tulathromycin+Tx, ceftiour+Tx, selamectin+Tx, carprofen+Tx,moxidectin+Tx, clorsulon+Tx, pyrantel+Tx, eprinomectin+Tx,doramectin+Tx, selamectin+Tx, nemadectin+Tx, albendazole+Tx,cambendazole+Tx, fenbendazole+Tx, flubendazole+Tx, mebendazole+Tx,oxfendazole+Tx, oxibendazole+Tx, parbendazole+Tx, tetramisole+Tx,levamisole+Tx, pyrantel pamoate+Tx, oxantel+Tx, morantel+Tx,triclabendazole+Tx, epsiprantel+Tx, lufenuron+Tx or ecdysone+Tx; evenmore preferably enrofloxacin+Tx, praziquantel+Tx, pyrantel embonate+Tx,febantel+Tx, penethamate+Tx, moloxicam+Tx, cefalexin+Tx, kanamycin+Tx,pimobendan+Tx, clenbuterol+Tx, omeprazole+Tx, tiamulin+Tx,benazepril+Tx, pyriprole+Tx, cefquinome+Tx, florfenicol+Tx,buserelin+Tx, cefovecin+Tx, tulathromycin+Tx, ceftiour+Tx,selamectin+Tx, carprofen+Tx, moxidectin+Tx, clorsulon+Tx or pyrantel+Tx.

Examples of ratios include 100:1 to 1:6000, 50:1 to 1:50, 20:1 to 1:20,even more especially from 10:1 to 1:10, 5:1 to 1:5, 2:1 to 1:2, 4:1 to2:1, 1:1, or 5:1, or 5:2, or 5:3, or 5:4, or 4:1, or 4:2, or 4:3, or3:1, or 3:2, or 2:1, or 1:5, or 2:5, or 3:5, or 4:5, or 1:4, or 2:4, or3:4, or 1:3, or 2:3, or 1:2, or 1:600, or 1:300, or 1:150, or 1:35, or2:35, or 4:35, or 1:75, or 2:75, or 4:75, or 1:6000, or 1:3000, or1:1500, or 1:350, or 2:350, or 4:350, or 1:750, or 2:750, or 4:750.Those mixing ratios are understood to include, on the one hand, ratiosby weight and also, on the other hand, molar ratios.

Of particular note is a combination where the additional activeingredient has a different site of action from the compound of formulaI. In certain instances, a combination with at least one other parasiticinvertebrate pest control active ingredient having a similar spectrum ofcontrol but a different site of action will be particularly advantageousfor resistance management. Thus, a combination product of the inventionmay comprise a pesticidally effective amount of a compound of formula Iand pesticidally effective amount of at least one additional parasiticinvertebrate pest control active ingredient having a similar spectrum ofcontrol but a different site of action.

One skilled in the art recognizes that because in the environment andunder physiological conditions salts of chemical compounds are inequilibrium with their corresponding non salt forms, salts share thebiological utility of the non salt forms.

Thus a wide variety of salts of compounds of the invention (and activeingredients used in combination with the active ingredients of theinvention) may be useful for control of invertebrate pests and animalparasites. Salts include acid-addition salts with inorganic or organicacids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric,acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic,salicylic, tartaric, 4-toluenesulfonic or valeric acids. The compoundsof the invention also include N-oxides. Accordingly, the inventioncomprises combinations of compounds of the invention including N-oxidesand salts thereof and an additional active ingredient including N-oxidesand salts thereof.

The compositions for use in animal health may also contain formulationauxiliaries and additives, known to those skilled in the art asformulation aids (some of which may be considered to also function assolid diluents, liquid diluents or surfactants). Such formulationauxiliaries and additives may control: pH (buffers), foaming duringprocessing (antifoams such polyorganosiloxanes), sedimentation of activeingredients (suspending agents), viscosity (thixotropic thickeners),in-container microbial growth (antimicrobials), product freezing(antifreezes), color (dyes/pigment dispersions), wash-off (film formersor stickers), evaporation (evaporation retardants), and otherformulation attributes. Film formers include, for example, polyvinylacetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinylacetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers andwaxes. Examples of formulation auxiliaries and additives include thoselisted in McCutcheon's Volume 2: Functional Materials, annualInternational and North American editions published by McCutcheon'sDivision, The Manufacturing Confectioner Publishing Co.; and PCTPublication WO 03/024222.

The compounds of the invention can be applied without other adjuvants,but most often application will be of a formulation comprising one ormore active ingredients with suitable carriers, diluents, andsurfactants and possibly in combination with a food depending on thecontemplated end use. One method of application involves spraying awater dispersion or refined oil solution of the combination products.Compositions with spray oils, spray oil concentrations, spreaderstickers, adjuvants, other solvents, and synergists such as piperonylbutoxide often enhance compound efficacy. Such sprays can be appliedfrom spray containers such as a can, a bottle or other container, eitherby means of a pump or by releasing it from a pressurized container,e.g., a pressurized aerosol spray can. Such spray compositions can takevarious forms, for example, sprays, mists, foams, fumes or fog. Suchspray compositions thus can further comprise propellants, foamingagents, etc. as the case may be. Of note is a spray compositioncomprising a pesticidally effective amount of a compound of theinvention and a carrier. One embodiment of such a spray compositioncomprises a pesticidally effective amount of a compound of the inventionand a propellant. Representative propellants include, but are notlimited to, methane, ethane, propane, butane, isobutane, butene,pentane, isopentane, neopentane, pentene, hydrofluorocarbons,chlorofluorocarbons, dimethyl ether, and mixtures of the foregoing. Ofnote is a spray composition (and a method utilizing such a spraycomposition dispensed from a spray container) used to control at leastone parasitic invertebrate pest selected from the group consisting ofmosquitoes, black flies, stable flies, deer flies, horse flies, wasps,yellow jackets, hornets, ticks, spiders, ants, gnats, and the like,including individually or in combinations.

The controlling of animal parasites includes controlling externalparasites that are parasitic to the surface of the body of the hostanimal (e.g., shoulders, armpits, abdomen, inner part of the thighs) andinternal parasites that are parasitic to the inside of the body of thehost animal (e.g., stomach, intestine, lung, veins, under the skin,lymphatic tissue). External parasitic or disease transmitting pestsinclude, for example, chiggers, ticks, lice, mosquitoes, flies, mitesand fleas. Internal parasites include heartworms, hookworms andhelminths. The compounds of the invention may be particularly suitablefor combating external parasitic pests. The compounds of the inventionmay be suitable for systemic and/or non-systemic control of infestationor infection by parasites on animals.

The compounds of the invention may be suitable for combating parasiticinvertebrate pests that infest animal subjects including those in thewild, livestock and agricultural working animals. Livestock is the termused to refer (singularly or plurally) to a domesticated animalintentionally reared in an agricultural setting to make produce such asfood or fiber, or for its labor; examples of livestock include cattle,sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, hens,turkeys, ducks and geese (e.g., raised for meat, milk, butter, eggs,fur, leather, feathers and/or wool). By combating parasites, fatalitiesand performance reduction (in terms of meat, milk, wool, skins, eggs,etc.) are reduced, so that applying the compounds of the inventionallows more economic and simple husbandry of animals.

The compounds of the invention may be suitable for combating parasiticinvertebrate pests that infest companion animals and pets (e.g., dogs,cats, pet birds and aquarium fish), research and experimental animals(e.g., hamsters, guinea pigs, rats and mice), as well as animals raisedfor/in zoos, wild habitats and/or circuses.

In an embodiment of this invention, the animal is preferably avertebrate, and more preferably a mammal, avian or fish. In a particularembodiment, the animal subject is a mammal (including great apes, suchas humans). Other mammalian subjects include primates (e.g., monkeys),bovine (e.g., cattle or dairy cows), porcine (e.g., hogs or pigs), ovine(e.g., goats or sheep), equine (e.g., horses), canine (e.g., dogs),feline (e.g., house cats), camels, deer, donkeys, buffalos, antelopes,rabbits, and rodents (e.g., guinea pigs, squirrels, rats, mice, gerbils,and hamsters). Avians include Anatidae (swans, ducks and geese),Columbidae (e.g., doves and pigeons), Phasianidae (e.g., partridges,grouse and turkeys), Thesienidae (e.g., domestic chickens), Psittacines(e.g., parakeets, macaws, and parrots), game birds, and ratites (e.g.,ostriches).

Birds treated or protected by the compounds of the invention can beassociated with either commercial or noncommercial aviculture. Theseinclude Anatidae, such as swans, geese, and ducks, Columbidae, such asdoves and domestic pigeons, Phasianidae, such as partridge, grouse andturkeys, Thesienidae, such as domestic chickens, and Psittacines, suchas parakeets, macaws and parrots raised for the pet or collector market,among others.

For purposes of the present invention, the term “fish” is understood toinclude without limitation, the Teleosti grouping of fish, i.e.,teleosts. Both the Salmoniformes order (which includes the Salmonidaefamily) and the Perciformes order (which includes the Centrarchidaefamily) are contained within the Teleosti grouping. Examples ofpotential fish recipients include the Salmonidae, Serranidae, Sparidae,Cichlidae, and Centrarchidae, among others.

Other animals are also contemplated to benefit from the inventivemethods, including marsupials (such as kangaroos), reptiles (such asfarmed turtles), and other economically important domestic animals forwhich the inventive methods are safe and effective in treating orpreventing parasite infection or infestation.

Examples of parasitic invertebrate pests controlled by administering apesticidally effective amount of the compounds of the invention to ananimal to be protected include ectoparasites (arthropods, acarines,etc.) and endoparasites (helminths, e.g., nematodes, trematodes,cestodes, acanthocephalans, etc.).

The disease or group of diseases described generally as helminthiasis isdue to infection of an animal host with parasitic worms known ashelminths. The term ‘helminths’ is meant to include nematodes,trematodes, cestodes and acanthocephalans. Helminthiasis is a prevalentand serious economic problem with domesticated animals such as swine,sheep, horses, cattle, goats, dogs, cats and poultry.

Among the helminths, the group of worms described as nematodes causeswidespread and at times serious infection in various species of animals.

Nematodes that are contemplated to be treated by the compounds of theinvention include, without limitation, the following genera:Acanthocheilonema, Aelurostrongylus, Ancylostoma, Angiostrongylus,Ascaridia, Ascaris, Brugia, Bunostomum, Capillaria, Chabertia, Cooperia,Crenosoma, Dictyocaulus, Dioctophyme, Dipetalonema, Diphyllobothrium,Dirofilaria, Dracunculus, Enterobius, Filaroides, Haemonchus, Heterakis,Lagochilascaris, Loa, Mansonella, Muellerius, Necator, Nematodirus,Oesophagostomum, Ostertagia, Oxyuris, Parafilaria, Parascaris,Physaloptera, Protostrongylus, Setaria, Spirocerca, Stephanofilaria,Strongyloides, Strongylus, Thelazia, Toxascaris, Toxocara, Trichinella,Trichonema, Trichostrongylus, Trichuris, Uncinaria and Wuchereria.

Of the above, the most common genera of nematodes infecting the animalsreferred to above are Haemonchus, Trichostrongylus, Ostertagia,Nematodirus, Cooperia, Ascaris, Bunostomum, Oesophagostomum, Chabertia,Trichuris, Strongylus, Trichonema, Dictyocaulus, Capillaria, Heterakis,Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria, Toxascaris andParascaris. Certain of these, such as Nematodirus, Cooperia andOesophagostomum attack primarily the intestinal tract while others, suchas Haemonchus and Ostertagia, are more prevalent in the stomach whileothers such as Dictyocaulus are found in the lungs. Still otherparasites may be located in other tissues such as the heart and bloodvessels, subcutaneous and lymphatic tissue and the like.

Trematodes that are contemplated to be treated by the invention and bythe inventive methods include, without limitation, the following genera:Alaria, Fasciola, Nanophyetus, Opisthorchis, Paragonimus andSchistosoma.

Cestodes that are contemplated to be treated by the invention and by theinventive methods include, without limitation, the following genera:Diphyllobothrium, Diplydium, Spirometra and Taenia.

The most common genera of parasites of the gastrointestinal tract ofhumans are

Ancylostoma, Necator, Ascaris, Strongy hides, Trichinella, Capillaria,Trichuris and Enterobius. Other medically important genera of parasiteswhich are found in the blood or other tissues and organs outside thegastrointestinal tract are the filarial worms such as Wuchereria,Brugia, Onchocerca and Loa, as well as Dracunculus and extra intestinalstages of the intestinal worms Strongyloides and Trichinella.

Numerous other helminth genera and species are known to the art, and arealso contemplated to be treated by the compounds of the invention. Theseare enumerated in great detail in Textbook of Veterinary ClinicalParasitology, Volume 1, Helminths, E. J. L. Soulsby, F. A. Davis Co.,Philadelphia, Pa.; Helminths, Arthropods and Protozoa, (6^(th) Editionof Monnig's Veterinary Helminthology and Entomology), E. J. L. Soulsby,Williams and Wilkins Co., Baltimore, Md.

The compounds of the invention may be effective against a number ofanimal ectoparasites (e.g., arthropod ectoparasites of mammals andbirds).

Insect and acarine pests include, e.g., biting insects such as flies andmosquitoes, mites, ticks, lice, fleas, true bugs, parasitic maggots, andthe like.

Adult flies include, e.g., the horn fly or Haematobia irritans, thehorse fly or Tabanus spp., the stable fly or Stomoxys calcitrans, theblack fly or Simulium spp., the deer fly or Chrysops spp., the louse flyor Melophagus ovinus, and the tsetse fly or Glossina spp. Parasitic flymaggots include, e.g., the bot fly (Oestrus ovis and Cuterebra spp.),the blow fly or Phaenicia spp., the screwworm or Cochliomyiahominivorax, the cattle grub or Hypoderma spp., the fleeceworm and theGastrophilus of horses. Mosquitoes include, for example, Culex spp.,Anopheles spp., and Aedes spp.

Mites include Mesostigmalphatalpha spp., e.g., mesostigmatids such asthe chicken mite, Dermalphanyssus galphallinalphae; itch or scab mitessuch as Sarcoptidae spp., for example, Salpharcoptes scalphabiei; mangemites such as Psoroptidae spp., including Chorioptes bovis and Psoroptesovis; chiggers e.g., Trombiculidae spp., for example the North Americanchigger, Trombiculalpha alphalfreddugesi.

Ticks include, e.g., soft-bodied ticks including Argasidae spp., forexample Argalphas spp., and Ornithodoros spp.; hard-bodied ticksincluding Ixodidae spp., for example Rhipicephalphalus sanguineus,Dermacentor variabilis, Dermacentor andersoni, Amblyomma americanum,Ixodes scapularis and other Rhipicephalus spp., (including the formerBoophilus genera).

Lice include, e.g., sucking lice, e.g., Menopon spp.

and Bovicola spp.; biting lice, e.g., Haematopinus spp., Linognathusspp., and Solenopotes spp.

Fleas include, e.g., Ctenocephalides spp., such as dog flea(Ctenocephalides canis) and cat flea (Ctenocephalides felis); Xenopsyllaspp., such as oriental rat flea (Xenopsylla cheopis); and Pulex spp.,such as human flea (Pulex irritans).

True bugs include, e.g., Cimicidae or e.g., the common bed bug (Cimexlectularius); Triatominae spp., including triatomid bugs also known askissing bugs; for example Rhodnius prolixus and Triatoma spp.

Generally, flies, fleas, lice, mosquitoes, gnats, mites, ticks andhelminths cause tremendous losses to the livestock and companion animalsectors. Arthropod parasites also are a nuisance to humans and canvector disease-causing organisms in humans and animals.

Numerous other parasitic invertebrate pests are known to the art, andare also contemplated to be treated by the compounds of the invention.These are enumerated in great detail in Medical and VeterinaryEntomology, D. S. Kettle, John Wiley AND Sons, New York and Toronto;Control of Arthropod Pests of Livestock: A Review of Technology, R. O.Drummand, J. E. George, and S. E. Kunz, CRC Press, Boca Raton, Fla.

The compounds of the invention may also be effective againstectoparasites including: flies such as Haematobia (Lyperosia) irritans(horn fly), Simulium spp., (blackfly), Glossina spp., (tsetse flies),Hydrotaea irritans (head fly), Musca autumnalis (face fly), Muscadomestica (house fly), Morellia simplex (sweat fly), Tabanus spp.,(horse fly), Hypoderma bovis, Hypoderma lineatum, Lucilia sericata,Lucilia cuprina (green blowfly), Calliphora spp., (blowfly),Protophormia spp., Oestrus ovis (nasal botfly), Culicoides spp.,(midges), Hippobosca equine, Gastrophilus intestinalis, Gastrophilushaemorrhoidalis and Gastrophilus nasalis; lice such as Bovicola(Damalinia) bovis, Bovicola equi, Haematopinus asini, Felicolasubrostratus, Heterodoxus spiniger, Lignonathus setosus and Trichodectescanis; keds such as Melophagus ovinus; and mites such as Psoroptes spp.,Sarcoptes scabei, Chorioptes bovis, Demodex equi, Cheyletiella spp.,Notoedres cati, Trombicula spp., and Otodectes cyanotis (ear mites).

Treatments of the invention are by conventional means such as by enteraladministration in the form of, for example, tablets, capsules, drinks,drenching preparations, granulates, pastes, boli, feed-throughprocedures, or suppositories; or by parenteral administration, such as,for example, by injection (including intramuscular, subcutaneous,intravenous, intraperitoneal) or implants; or by nasal administration.

When compounds of the invention are applied in combination with anadditional biologically active ingredient, they may be administeredseparately e.g. as separate compositions. In this case, the biologicallyactive ingredients may be administered simultaneously or sequentially.Alternatively, the biologically active ingredients may be components ofone composition.

The compounds of the invention may be administered in a controlledrelease form, for example in subcutaneous or orally adminstered slowrelease formulations.

Typically a parasiticidal composition according to the present inventioncomprises a compound of the invention, optionally in combination with anadditional biologically active ingredient, or N-oxides or salts thereof,with one or more pharmaceutically or veterinarily acceptable carrierscomprising excipients and auxiliaries selected with regard to theintended route of administration (e.g., oral or parenteraladministration such as injection) and in accordance with standardpractice. In addition, a suitable carrier is selected on the basis ofcompatibility with the one or more active ingredients in thecomposition, including such considerations as stability relative to pHand moisture content. Therefore of note are compounds of the inventionfor protecting an animal from an invertebrate parasitic pest comprisinga parasitically effective amount of a compound of the invention,optionally in combination with an additional biologically activeingredient and at least one carrier.

For parenteral administration including intravenous, intramuscular andsubcutaneous injection, the compounds of the invention can be formulatedin suspension, solution or emulsion in oily or aqueous vehicles, and maycontain adjuncts such as suspending, stabilizing and/or dispersingagents.

The compounds of the invention may also be formulated for bolusinjection or continuous infusion. Pharmaceutical compositions forinjection include aqueous solutions of water-soluble forms of activeingredients (e.g., a salt of an active compound), preferably inphysiologically compatible buffers containing other excipients orauxiliaries as are known in the art of pharmaceutical formulation.Additionally, suspensions of the active compounds may be prepared in alipophilic vehicle. Suitable lipophilic vehicles include fatty oils suchas sesame oil, synthetic fatty acid esters such as ethyl oleate andtriglycerides, or materials such as liposomes.

Aqueous injection suspensions may contain substances that increase theviscosity of the suspension, such as sodium carboxymethyl cellulose,sorbitol, or dextran. Formulations for injection may be presented inunit dosage form, e.g., in ampoules or in multi-dose containers.Alternatively, the active ingredient may be in powder form forconstitution with a suitable vehicle, e.g., sterile, pyrogen-free water,before use.

In addition to the formulations described supra, the compounds of theinvention may also be formulated as a depot preparation. Such longacting formulations may be administered by implantation (for example,subcutaneously or intramuscularly) or by intramuscular or subcutaneousinjection.

The compounds of the invention may be formulated for this route ofadministration with suitable polymeric or hydrophobic materials (forinstance, in an emulsion with a pharmacologically acceptable oil), withion exchange resins, or as a sparingly soluble derivative such as,without limitation, a sparingly soluble salt.

For administration by inhalation, the compounds of the invention can bedelivered in the form of an aerosol spray using a pressurized pack or anebulizer and a suitable propellant, e.g., without limitation,dichlorodifluoromethane, trichlorofluoromethane,dichlorotetrafluoroethane or carbon dioxide. In the case of apressurized aerosol, the dosage unit may be controlled by providing avalve to deliver a metered amount.

Capsules and cartridges of, for example, gelatin for use in an inhaleror insufflator may be formulated containing a powder mix of the compoundand a suitable powder base such as lactose or starch.

The compounds of the invention may have favourable pharmacokinetic andpharmacodynamic properties providing systemic availability from oraladministration and ingestion. Therefore after ingestion by the animal tobe protected, parasiticidally effective concentrations of a compound ofthe invention in the bloodstream may protect the treated animal fromblood-sucking pests such as fleas, ticks and lice. Therefore of note isa composition for protecting an animal from an invertebrate parasitepest in a form for oral administration (i.e. comprising, in addition toa parasiticidally effective amount of a compound of the invention, oneor more carriers selected from binders and fillers suitable for oraladministration and feed concentrate carriers).

For oral administration in the form of solutions (the most readilyavailable form for absorption), emulsions, suspensions, pastes, gels,capsules, tablets, boluses, powders, granules, rumen-retention andfeed/water/lick blocks, the compounds of the invention can be formulatedwith binders/fillers known in the art to be suitable for oraladministration compositions, such as sugars and sugar derivatives (e.g.,lactose, sucrose, mannitol, sorbitol), starch (e.g., maize starch, wheatstarch, rice starch, potato starch), cellulose and derivatives (e.g.,methylcellulose, carboxymethylcellulose, ethylhydroxycellulose), proteinderivatives (e.g., zein, gelatin), and synthetic polymers (e.g.,polyvinyl alcohol, polyvinylpyrrolidone). If desired, lubricants (e.g.,magnesium stearate), disintegrating agents (e.g., cross-linkedpolyvinylpyrrolidinone, agar, alginic acid) and dyes or pigments can beadded. Pastes and gels often also contain adhesives (e.g., acacia,alginic acid, bentonite, cellulose, xanthan gum, colloidal magnesiumaluminum silicate) to aid in keeping the composition in contact with theoral cavity and not being easily ejected.

In one embodiment a composition of the present invention is formulatedinto a chewable and/or edible product (e.g., a chewable treat or edibletablet). Such a product would ideally have a taste, texture and/or aromafavored by the animal to be protected so as to facilitate oraladministration of the compounds of the invention.

If the parasiticidal compositions are in the form of feed concentrates,the carrier is typically selected from high-performance feed, feedcereals or protein concentrates.

Such feed concentrate-containing compositions can, in addition to theparasiticidal active ingredients, comprise additives promoting animalhealth or growth, improving quality of meat from animals for slaughteror otherwise useful to animal husbandry.

These additives can include, for example, vitamins, antibiotics,chemotherapeutics, bacteriostats, fungistats, coccidiostats andhormones.

The compound of the invention may also be formulated in rectalcompositions such as suppositories or retention enemas, using, e.g.,conventional suppository bases such as cocoa butter or other glycerides.

The formulations for the method of this invention may include anantioxidant, such as BHT (butylated hydroxytoluene). The antioxidant isgenerally present in amounts of at 0.1-5 percent (wt/vol). Some of theformulations require a solubilizer, such as oleic acid, to dissolve theactive agent, particularly if spinosad is included. Common spreadingagents used in these pour-on formulations include isopropyl myristate,isopropyl palmitate, caprylic/capric acid esters of saturated C₁₂-C₁₈fatty alcohols, oleic acid, oleyl ester, ethyl oleate, triglycerides,silicone oils and dipropylene glycol methyl ether. The pour-onformulations for the method of this invention are prepared according toknown techniques. Where the pour-on is a solution, theparasiticide/insecticide is mixed with the carrier or vehicle, usingheat and stirring if required. Auxiliary or additional ingredients canbe added to the mixture of active agent and carrier, or they can bemixed with the active agent prior to the addition of the carrier.Pour-on formulations in the form of emulsions or suspensions aresimilarly prepared using known techniques.

Other delivery systems for relatively hydrophobic pharmaceuticalcompounds may be employed. Liposomes and emulsions are well-knownexamples of delivery vehicles or carriers for hydrophobic drugs. Inaddition, organic solvents such as dimethylsulfoxide may be used, ifneeded.

The rate of application required for effective parasitic invertebratepest control (e.g. “pesticidally effective amount”) will depend on suchfactors as the species of parasitic invertebrate pest to be controlled,the pest's life cycle, life stage, its size, location, time of year,host crop or animal, feeding behavior, mating behavior, ambientmoisture, temperature, and the like. One skilled in the art can easilydetermine the pesticidally effective amount necessary for the desiredlevel of parasitic invertebrate pest control.

In general for veterinary use, the compounds of the invention areadministered in a pesticidally effective amount to an animal,particularly a homeothermic animal, to be protected from parasiticinvertebrate pests.

A pesticidally effective amount is the amount of active ingredientneeded to achieve an observable effect diminishing the occurrence oractivity of the target parasitic invertebrate pest. One skilled in theart will appreciate that the pesticidally effective dose can vary forthe various compounds and compositions useful for the method of thepresent invention, the desired pesticidal effect and duration, thetarget parasitic invertebrate pest species, the animal to be protected,the mode of application and the like, and the amount needed to achieve aparticular result can be determined through simple experimentation.

For oral or parenteral administration to animals, a dose of thecompositions of the present invention administered at suitable intervalstypically ranges from about 0.01 mg/kg to about 100 mg/kg, andpreferably from about 0.01 mg/kg to about 30 mg/kg of animal bodyweight.

Suitable intervals for the administration of the compositions of thepresent invention to animals range from about daily to about yearly. Ofnote are administration intervals ranging from about weekly to aboutonce every 6 months. Of particular note are monthly administrationintervals (i.e. administering the compounds to the animal once everymonth). The present invention also provides a method for controllingpests (such as mosquitoes and other disease vectors; see alsohttp://www.who.int/malaria/vector_control/irs/en/). In one embodiment,the method for controlling pests comprises applying the compositions ofthe invention to the target pests, to their locus or to a surface orsubstrate by brushing, rolling, spraying, spreading or dipping. By wayof example, an IRS (indoor residual spraying) application of a surfacesuch as a wall, ceiling or floor surface is contemplated by the methodof the invention. In another embodiment, it is contemplated to applysuch compositions to a substrate such as non-woven or a fabric materialin the form of (or which can be used in the manufacture of) netting,clothing, bedding, curtains and tents.

In one embodiment, the method for controlling such pests comprisesapplying a pesticidally effective amount of the compositions of theinvention to the target pests, to their locus, or to a surface orsubstrate so as to provide effective residual pesticidal activity on thesurface or substrate. Such application may be made by brushing, rolling,spraying, spreading or dipping the pesticidal composition of theinvention. By way of example, an IRS application of a surface such as awall, ceiling or floor surface is contemplated by the method of theinvention so as to provide effective residual pesticidal activity on thesurface. In another embodiment, it is contemplated to apply suchcompositions for residual control of pests on a substrate such as afabric material in the form of (or which can be used in the manufactureof) netting, clothing, bedding, curtains and tents.

Substrates including non-woven, fabrics or netting to be treated may bemade of natural fibres such as cotton, raffia, jute, flax, sisal,hessian, or wool, or synthetic fibres such as polyamide, polyester,polypropylene, polyacrylonitrile or the like. The polyesters areparticularly suitable. The methods of textile treatment are know, e.g.from Handbuch Textilveredlung: Band 1: Ausrüstung, Band 2: Farbgebung,Band 3: Beschichtung, Band 4: Umwelttechnik; Verlag: DeutscherFachverlag; Auflage: 15, überarbeitete Ausgabe (17. Apr. 2006); ISBN-10:3866410123; ISBN-13: 978-3866410121, see especially Band 1: Ausrüstungpages 27-198, more preferably on page 118; or WO2008151984 orWO2003034823 or U.S. Pat. No. 5,631,072 or WO200564072 or WO2006128870or EP1724392 or WO2005064072 or WO2005113886 or WO2007090739.

The term “plant” as used herein includes seedlings, bushes and trees.

The term “crops” or “plant” is to be understood as including also cropplants which have been so transformed by the use of recombinant DNAtechniques that they are capable of synthesising one or more selectivelyacting toxins, such as are known, for example, from toxin-producingbacteria, especially those of the genus Bacillus.

Toxins that can be expressed by such transgenic plants include, forexample, insecticidal proteins, from Bacillus cereus or Bacilluspopilliae; or insecticidal proteins from Bacillus thuringiensis, such asδ-endotoxins, e.g. Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A,Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), e.g. Vip1,Vip2, Vip3 or Vip3A; or insecticidal proteins of bacteria colonisingnematodes, for example Photorhabdus spp., or Xenorhabdus spp., such asPhotorhabdus luminescens, Xenorhabdus nematophilus; toxins produced byanimals, such as scorpion toxins, arachnid toxins, wasp toxins and otherinsect-specific neurotoxins; toxins produced by fungi, such asStreptomycetes toxins, plant lectins, such as pea lectins, barleylectins or snowdrop lectins; agglutinins; proteinase inhibitors, such astrypsin inhibitors, serine protease inhibitors, patatin, cystatin,papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin,maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolismenzymes, such as 3-hydroxysteroidoxidase,ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidases, ecdysoneinhibitors, HMG-COA-reductase, ion channel blockers, such as blockers ofsodium or calcium channels, juvenile hormone esterase, diuretic hormonereceptors, stilbene synthase, bibenzyl synthase, chitinases andglucanases.

In the context of the present invention there are to be understood byδ-endotoxins, for example Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A,Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for exampleVip1, Vip2, Vip3 or Vip3A, expressly also hybrid toxins, truncatedtoxins and modified toxins. Hybrid toxins are produced recombinantly bya new combination of different domains of those proteins (see, forexample, WO 02/15701). Truncated toxins, for example a truncated Cry1Ab,are known. In the case of modified toxins, one or more amino acids ofthe naturally occurring toxin are replaced. In such amino acidreplacements, preferably non-naturally present protease recognitionsequences are inserted into the toxin, such as, for example, in the caseof Cry3A055, a cathepsin-G-recognition sequence is inserted into a Cry3Atoxin (see WO 03/018810).

Examples of such toxins or transgenic plants capable of synthesisingsuch toxins are disclosed, for example, in EP-A-0 374 753, WO 93/07278,WO 95/34656, EP-A-0 427 529, EP-A-451 878 and WO 03/052073.

The processes for the preparation of such transgenic plants aregenerally known to the person skilled in the art and are described, forexample, in the publications mentioned above. CryI-type deoxyribonucleicacids and their preparation are known, for example, from WO 95/34656,EP-A-0 367 474, EP-A-0 401 979 and WO 90/13651.

The toxin contained in the transgenic plants imparts to the plantstolerance to harmful insects. Such insects can occur in any taxonomicgroup of insects, but are especially commonly found in the beetles(Coleoptera), two-winged insects (Diptera) and butterflies(Lepidoptera). Transgenic plants containing one or more genes that codefor an insecticidal resistance and express one or more toxins are knownand some of them are commercially available. Examples of such plantsare: YieldGard® (maize variety that expresses a Cry1Ab toxin); YieldGardRootworm® (maize variety that expresses a Cry3Bb1 toxin); YieldGardPlus® (maize variety that expresses a Cry1Ab and a Cry3Bb1 toxin);Starlink® (maize variety that expresses a Cry9C toxin); Herculex I®(maize variety that expresses a Cry1Fa2 toxin and the enzymephosphinothricine N-acetyltransferase (PAT) to achieve tolerance to theherbicide glufosinate ammonium); NuCOTN 33B® (cotton variety thatexpresses a Cry1Ac toxin); Bollgard I® (cotton variety that expresses aCry1Ac toxin); Bollgard II® (cotton variety that expresses a Cry1Ac anda Cry2Ab toxin); VipCot® (cotton variety that expresses a Vip3A and aCry1Ab toxin); NewLeaf® (potato variety that expresses a Cry3A toxin);NatureGard®, Agrisure® GT Advantage (GA21 glyphosate-tolerant trait),Agrisure® CB Advantage (Bt11 corn borer (CB) trait) and Protecta®.

Further examples of such transgenic crops are:

1. Bt11 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790St. Sauveur, France, registration number C/FR/96/05/10. Geneticallymodified Zea mays which has been rendered resistant to attack by theEuropean corn borer (Ostrinia nubilalis and Sesamia nonagrioides) bytransgenic expression of a truncated Cry1Ab toxin. Bt11 maize alsotransgenically expresses the enzyme PAT to achieve tolerance to theherbicide glufosinate ammonium.

2. Bt176 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790St. Sauveur, France, registration number C/FR/96/05/10. Geneticallymodified Zea mays which has been rendered resistant to attack by theEuropean corn borer (Ostrinia nubilalis and Sesamia nonagrioides) bytransgenic expression of a Cry1Ab toxin. Bt176 maize also transgenicallyexpresses the enzyme PAT to achieve tolerance to the herbicideglufosinate ammonium.

3. MIR604 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790St. Sauveur, France, registration number C/FR/96/05/10. Maize which hasbeen rendered insect-resistant by transgenic expression of a modifiedCry3A toxin. This toxin is Cry3A055 modified by insertion of acathepsin-G-protease recognition sequence. The preparation of suchtransgenic maize plants is described in WO 03/018810.

4. MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren,B-1150 Brussels, Belgium, registration number C/DE/02/9. MON 863expresses a Cry3Bb1 toxin and has resistance to certain Coleopterainsects.

5. IPC 531 Cotton from Monsanto Europe S.A. 270-272 Avenue de Tervuren,B-1150 Brussels, Belgium, registration number C/ES/96/02.

6. 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7B-1160 Brussels, Belgium, registration number C/NL/00/10. Geneticallymodified maize for the expression of the protein Cry1F for achievingresistance to certain Lepidoptera insects and of the PAT protein forachieving tolerance to the herbicide glufosinate ammonium.

7. NK603×MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue deTervuren, B-1150 Brussels, Belgium, registration number C/GB/02/M3/03.Consists of conventionally bred hybrid maize varieties by crossing thegenetically modified varieties NK603 and MON 810. NK603×MON 810 Maizetransgenically expresses the protein CP4 EPSPS, obtained fromAgrobacterium spp. strain CP4, which imparts tolerance to the herbicideRoundup® (contains glyphosate), and also a Cry1Ab toxin obtained fromBacillus thuringiensis subsp. kurstaki which brings about tolerance tocertain Lepidoptera, include the European corn borer.

The activity of the compositions according to the invention can bebroadened considerably, and adapted to prevailing circumstances, byadding other insecticidally, acaricidally and/or fungicidally activeingredients. The mixtures of the compounds of formula I with otherinsecticidally, acaricidally and/or fungicidally active ingredients mayalso have further surprising advantages which can also be described, ina wider sense, as synergistic activity. For example, better tolerance byplants, reduced phytotoxicity, insects can be controlled in theirdifferent development stages or better behaviour during theirproduction, for example during grinding or mixing, during their storageor during their use.

Suitable additions to active ingredients here are, for example,representatives of the following classes of active ingredients:organophosphorus compounds, nitrophenol derivatives, thioureas, juvenilehormones, formamidines, benzophenone derivatives, ureas, pyrrolederivatives, carbamates, pyrethroids, chlorinated hydrocarbons,acylureas, pyridyl-methyleneamino derivatives, macrolides,neonicotinoids and Bacillus thuringiensis preparations.

The following mixtures of the compounds of formula I with activeingredients are preferred (the abbreviation “TX” means “one specific thecompound of the formula (I) or one specific compound selected from theTable A1 to A12 and Table B:

an adjuvant selected from the group of substances consisting ofpetroleum oils (alternative name) (628)+TX,

an acaricide selected from the group of substances consisting of1,1-bis(4-chlorophenyl)-2-ethoxyethanol (IUPAC name) (910)+TX,2,4-dichlorophenyl benzenesulfonate (IUPAC/Chemical Abstracts name)(1059)+TX, 2-fluoro-N-methyl-N-1-naphthylacetamide (IUPAC name)(1295)+TX, 4-chlorophenyl phenyl sulfone (IUPAC name) (981)+TX,abamectin (1)+TX, acequinocyl (3)+TX, acetoprole [CCN]+TX, acrinathrin(9)+TX, aldicarb (16)+TX, aldoxycarb (863)+TX, alpha-cypermethrin(202)+TX, amidithion (870)+TX, amidoflumet [CCN]+TX, amidothioate(872)+TX, amiton (875)+TX, amiton hydrogen oxalate (875)+TX, amitraz(24)+TX, aramite (881)+TX, arsenous oxide (882)+TX, AVI 382 (compoundcode)+TX, AZ 60541 (compound code)+TX, azinphos-ethyl (44)+TX,azinphos-methyl (45)+TX, azobenzene (IUPAC name) (888)+TX, azocyclotin(46)+TX, azothoate (889)+TX, benomyl (62)+TX, benoxafos (alternativename) [CCN]+TX, benzoximate (71)+TX, benzyl benzoate (IUPAC name)[CCN]+TX, bifenazate (74)+TX, bifenthrin (76)+TX, binapacryl (907)+TX,brofenvalerate (alternative name)+TX, bromocyclen (918)+TX, bromophos(920)+TX, bromophos-ethyl (921)+TX, bromopropylate (94)+TX, buprofezin(99)+TX, butocarboxim (103)+TX, butoxycarboxim (104)+TX, butylpyridaben(alternative name)+TX, calcium polysulfide (IUPAC name) (111)+TX,camphechlor (941)+TX, carbanolate (943)+TX, carbaryl (115)+TX,carbofuran (118)+TX, carbophenothion (947)+TX, CGA 50′439 (developmentcode) (125)+TX, chinomethionat (126)+TX, chlorbenside (959)+TX,chlordimeform (964)+TX, chlordimeform hydrochloride (964)+TX,chlorfenapyr (130)+TX, chlorfenethol (968)+TX, chlorfenson (970)+TX,chlorfensulphide (971)+TX, chlorfenvinphos (131)+TX, chlorobenzilate(975)+TX, chloromebuform (977)+TX, chloromethiuron (978)+TX,chloropropylate (983)+TX, chlorpyrifos (145)+TX, chlorpyrifos-methyl(146)+TX, chlorthiophos (994)+TX, cinerin I (696)+TX, cinerin II(696)+TX, cinerins (696)+TX, clofentezine (158)+TX, closantel(alternative name) [CCN]+TX, coumaphos (174)+TX, crotamiton (alternativename) [CCN]+TX, crotoxyphos (1010)+TX, cufraneb (1013)+TX, cyanthoate(1020)+TX, cyflumetofen (CAS Reg. No.: 400882-07-7)+TX, cyhalothrin(196)+TX, cyhexatin (199)+TX, cypermethrin (201)+TX, DCPM (1032)+TX, DDT(219)+TX, demephion (1037)+TX, demephion-O (1037)+TX, demephion-S(1037)+TX, demeton (1038)+TX, demeton-methyl (224)+TX, demeton-O(1038)+TX, demeton-O-methyl (224)+TX, demeton-S (1038)+TX,demeton-S-methyl (224)+TX, demeton-S-methylsulphon (1039)+TX,diafenthiuron (226)+TX, dialifos (1042)+TX, diazinon (227)+TX,dichlofluanid (230)+TX, dichlorvos (236)+TX, dicliphos (alternativename)+TX, dicofol (242)+TX, dicrotophos (243)+TX, dienochlor (1071)+TX,dimefox (1081)+TX, dimethoate (262)+TX, dinactin (alternative name)(653)+TX, dinex (1089)+TX, dinex-diclexine (1089)+TX, dinobuton(269)+TX, dinocap (270)+TX, dinocap-4 [CCN]+TX, dinocap-6 [CCN]+TX,dinocton (1090)+TX, dinopenton (1092)+TX, dinosulfon (1097)+TX,dinoterbon (1098)+TX, dioxathion (1102)+TX, diphenyl sulfone (IUPACname) (1103)+TX, disulfiram (alternative name) [CCN]+TX, disulfoton(278)+TX, DNOC (282)+TX, dofenapyn (1113)+TX, doramectin (alternativename) [CCN]+TX, endosulfan (294)+TX, endothion (1121)+TX, EPN (297)+TX,eprinomectin (alternative name) [CCN]+TX, ethion (309)+TX,ethoate-methyl (1134)+TX, etoxazole (320)+TX, etrimfos (1142)+TX,fenazaflor (1147)+TX, fenazaquin (328)+TX, fenbutatin oxide (330)+TX,fenothiocarb (337)+TX, fenpropathrin (342)+TX, fenpyrad (alternativename)+TX, fenpyroximate (345)+TX, fenson (1157)+TX, fentrifanil(1161)+TX, fenvalerate (349)+TX, fipronil (354)+TX, fluacrypyrim(360)+TX, fluazuron (1166)+TX, flubenzimine (1167)+TX, flucycloxuron(366)+TX, flucythrinate (367)+TX, fluenetil (1169)+TX, flufenoxuron(370)+TX, flumethrin (372)+TX, fluorbenside (1174)+TX, fluvalinate(1184)+TX, FMC 1137 (development code) (1185)+TX, formetanate (405)+TX,formetanate hydrochloride (405)+TX, formothion (1192)+TX, formparanate(1193)+TX, gamma-HCH (430)+TX, glyodin (1205)+TX, halfenprox (424)+TX,heptenophos (432)+TX, hexadecyl cyclopropanecarboxylate (IUPAC/ChemicalAbstracts name) (1216)+TX, hexythiazox (441)+TX, iodomethane (IUPACname) (542)+TX, isocarbophos (alternative name) (473)+TX, isopropylO-(methoxyaminothiophosphoryl)salicylate (IUPAC name) (473)+TX,ivermectin (alternative name) [CCN]+TX, jasmolin I (696)+TX, jasmolin II(696)+TX, jodfenphos (1248)+TX, lindane (430)+TX, lufenuron (490)+TX,malathion (492)+TX, malonoben (1254)+TX, mecarbam (502)+TX, mephosfolan(1261)+TX, mesulfen (alternative name) [CCN]+TX, methacrifos (1266)+TX,methamidophos (527)+TX, methidathion (529)+TX, methiocarb (530)+TX,methomyl (531)+TX, methyl bromide (537)+TX, metolcarb (550)+TX,mevinphos (556)+TX, mexacarbate (1290)+TX, milbemectin (557)+TX,milbemycin oxime (alternative name) [CCN]+TX, mipafox (1293)+TX,monocrotophos (561)+TX, morphothion (1300)+TX, moxidectin (alternativename) [CCN]+TX, naled (567)+TX, NC-184 (compound code)+TX, NC-512(compound code)+TX, nifluridide (1309)+TX, nikkomycins (alternativename) [CCN]+TX, nitrilacarb (1313)+TX, nitrilacarb 1:1 zinc chloridecomplex (1313)+TX, NNI-0101 (compound code)+TX, NNI-0250 (compoundcode)+TX, omethoate (594)+TX, oxamyl (602)+TX, oxydeprofos (1324)+TX,oxydisulfoton (1325)+TX, pp′-DDT (219)+TX, parathion (615)+TX,permethrin (626)+TX, petroleum oils (alternative name) (628)+TX,phenkapton (1330)+TX, phenthoate (631)+TX, phorate (636)+TX, phosalone(637)+TX, phosfolan (1338)+TX, phosmet (638)+TX, phosphamidon (639)+TX,phoxim (642)+TX, pirimiphos-methyl (652)+TX, polychloroterpenes(traditional name) (1347)+TX, polynactins (alternative name) (653)+TX,proclonol (1350)+TX, profenofos (662)+TX, promacyl (1354)+TX, propargite(671)+TX, propetamphos (673)+TX, propoxur (678)+TX, prothidathion(1360)+TX, prothoate (1362)+TX, pyrethrin I (696)+TX, pyrethrin II(696)+TX, pyrethrins (696)+TX, pyridaben (699)+TX, pyridaphenthion(701)+TX, pyrimidifen (706)+TX, pyrimitate (1370)+TX, quinalphos(711)+TX, quintiofos (1381)+TX, R-1492 (development code) (1382)+TX,RA-17 (development code) (1383)+TX, rotenone (722)+TX, schradan(1389)+TX, sebufos (alternative name)+TX, selamectin (alternative name)[CCN]+TX, SI-0009 (compound code)+TX, sophamide (1402)+TX, spirodiclofen(738)+TX, spiromesifen (739)+TX, SSI-121 (development code) (1404)+TX,sulfiram (alternative name) [CCN]+TX, sulfluramid (750)+TX, sulfotep(753)+TX, sulphur (754)+TX, SZI-121 (development code) (757)+TX,tau-fluvalinate (398)+TX, tebufenpyrad (763)+TX, TEPP (1417)+TX, terbam(alternative name)+TX, tetrachlorvinphos (777)+TX, tetradifon (786)+TX,tetranactin (alternative name) (653)+TX, tetrasul (1425)+TX, thiafenox(alternative name)+TX, thiocarboxime (1431)+TX, thiofanox (800)+TX,thiometon (801)+TX, thioquinox (1436)+TX, thuringiensin (alternativename) [CCN]+TX, triamiphos (1441)+TX, triarathene (1443)+TX, triazophos(820)+TX, triazuron (alternative name)+TX, trichlorfon (824)+TX,trifenofos (1455)+TX, trinactin (alternative name) (653)+TX, vamidothion(847)+TX, vaniliprole [CCN] and YI-5302 (compound code)+TX,

an algicide selected from the group of substances consisting ofbethoxazin [CCN]+TX, copper dioctanoate (IUPAC name) (170)+TX, coppersulfate (172)+TX, cybutryne [CCN]+TX, dichlone (1052)+TX, dichlorophen(232)+TX, endothal (295)+TX, fentin (347)+TX, hydrated lime [CCN]+TX,nabam (566)+TX, quinoclamine (714)+TX, quinonamid (1379)+TX, simazine(730)+TX, triphenyltin acetate (IUPAC name) (347) and triphenyltinhydroxide (IUPAC name) (347)+TX,

an anthelmintic selected from the group of substances consisting ofabamectin (1)+TX, crufomate (1011)+TX, doramectin (alternative name)[CCN]+TX, emamectin (291)+TX, emamectin benzoate (291)+TX, eprinomectin(alternative name) [CCN]+TX, ivermectin (alternative name) [CCN]+TX,milbemycin oxime (alternative name) [CCN]+TX, moxidectin (alternativename) [CCN]+TX, piperazine [CCN]+TX, selamectin (alternative name)[CCN]+TX, spinosad (737) and thiophanate (1435)+TX, an avicide selectedfrom the group of substances consisting of chloralose (127)+TX, endrin(1122)+TX, fenthion (346)+TX, pyridin-4-amine (IUPAC name) (23) andstrychnine (745)+TX,

a bactericide selected from the group of substances consisting of1-hydroxy-1H-pyridine-2-thione (IUPAC name) (1222)+TX,4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748)+TX,8-hydroxyquinoline sulfate (446)+TX, bronopol (97)+TX, copperdioctanoate (IUPAC name) (170)+TX, copper hydroxide (IUPAC name)(169)+TX, cresol [CCN]+TX, dichlorophen (232)+TX, dipyrithione(1105)+TX, dodicin (1112)+TX, fenaminosulf (1144)+TX, formaldehyde(404)+TX, hydrargaphen (alternative name) [CCN]+TX, kasugamycin(483)+TX, kasugamycin hydrochloride hydrate (483)+TX, nickelbis(dimethyldithiocarbamate) (IUPAC name) (1308)+TX, nitrapyrin(580)+TX, octhilinone (590)+TX, oxolinic acid (606)+TX, oxytetracycline(611)+TX, potassium hydroxyquinoline sulfate (446)+TX, probenazole(658)+TX, streptomycin (744)+TX, streptomycin sesquisulfate (744)+TX,tecloftalam (766)+TX, and thiomersal (alternative name) [CCN]+TX,

a biological agent selected from the group of substances consisting ofAdoxophyes orana GV (alternative name) (12)+TX, Agrobacteriumradiobacter (alternative name) (13)+TX, Amblyseius spp. (alternativename) (19)+TX, Anagrapha falcifera NPV (alternative name) (28)+TX,Anagrus atomus (alternative name) (29)+TX, Aphelinus abdominalis(alternative name) (33)+TX, Aphidius colemani (alternative name)(34)+TX, Aphidoletes aphidimyza (alternative name) (35)+TX, Autographacalifornica NPV (alternative name) (38)+TX, Bacillus firmus (alternativename) (48)+TX, Bacillus sphaericus Neide (scientific name) (49)+TX,Bacillus thuringiensis Berliner (scientific name) (51)+TX, Bacillusthuringiensis subsp. aizawai (scientific name) (51)+TX, Bacillusthuringiensis subsp. israelensis (scientific name) (51)+TX, Bacillusthuringiensis subsp. japonensis (scientific name) (51)+TX, Bacillusthuringiensis subsp. kurstaki (scientific name) (51)+TX, Bacillusthuringiensis subsp. tenebrionis (scientific name) (51)+TX, Beauveriabassiana (alternative name) (53)+TX, Beauveria brongniartii (alternativename) (54)+TX, Chrysoperla carnea (alternative name) (151)+TX,Cryptolaemus montrouzieri (alternative name) (178)+TX, Cydia pomonellaGV (alternative name) (191)+TX, Dacnusa sibirica (alternative name)(212)+TX, Diglyphus isaea (alternative name) (254)+TX, Encarsia formosa(scientific name) (293)+TX, Eretmocerus eremicus (alternative name)(300)+TX, Helicoverpa zea NPV (alternative name) (431)+TX,Heterorhabditis bacteriophora and H. megidis (alternative name)(433)+TX, Hippodamia convergens (alternative name) (442)+TX, Leptomastixdactylopii (alternative name) (488)+TX, Macrolophus caliginosus(alternative name) (491)+TX, Mamestra brassicae NPV (alternative name)(494)+TX, Metaphycus helvolus (alternative name) (522)+TX, Metarhiziumanisopliae var. acridum (scientific name) (523)+TX, Metarhiziumanisopliae var. anisopliae (scientific name) (523)+TX, Neodiprionsertifer NPV and N. lecontei NPV (alternative name) (575)+TX, Orius spp.(alternative name) (596)+TX, Paecilomyces fumosoroseus (alternativename) (613)+TX, Phytoseiulus persimilis (alternative name) (644)+TX,Spodoptera exigua multicapsid nuclear polyhedrosis virus (scientificname) (741)+TX, Steinernema bibionis (alternative name) (742)+TX,Steinernema carpocapsae (alternative name) (742)+TX, Steinernema feltiae(alternative name) (742)+TX, Steinernema glaseri (alternative name)(742)+TX, Steinernema riobrave (alternative name) (742)+TX, Steinernemariobravis (alternative name) (742)+TX, Steinernema scapterisci(alternative name) (742)+TX, Steinernema spp. (alternative name)(742)+TX, Trichogramma spp. (alternative name) (826)+TX, Typhlodromusoccidentalis (alternative name) (844) and Verticillium lecanii(alternative name) (848)+TX,

a soil sterilant selected from the group of substances consisting ofiodomethane (IUPAC name) (542) and methyl bromide (537)+TX,

a chemosterilant selected from the group of substances consisting ofapholate [CCN]+TX, bisazir (alternative name) [CCN]+TX, busulfan(alternative name) [CCN]+TX, diflubenzuron (250)+TX, dimatif(alternative name) [CCN]+TX, hemel [CCN]+TX, hempa [CCN]+TX, metepa[CCN]+TX, methiotepa [CCN]+TX, methyl apholate [CCN]+TX, morzid[CCN]+TX, penfluron (alternative name) [CCN]+TX, tepa [CCN]+TX,thiohempa (alternative name) [CCN]+TX, thiotepa (alternative name)[CCN]+TX, tretamine (alternative name) [CCN] and uredepa (alternativename) [CCN]+TX, an insect pheromone selected from the group ofsubstances consisting of (E)-dec-5-en-1-yl acetate with(E)-dec-5-en-1-ol (IUPAC name) (222)+TX, (E)-tridec-4-en-1-yl acetate(IUPAC name) (829)+TX, (E)-6-methylhept-2-en-4-ol (IUPAC name) (541)+TX,(E,Z)-tetradeca-4,10-dien-1-yl acetate (IUPAC name) (779)+TX,(Z)-dodec-7-en-1-yl acetate (IUPAC name) (285)+TX, (Z)-hexadec-11-enal(IUPAC name) (436)+TX, (Z)-hexadec-11-en-1-yl acetate (IUPAC name)(437)+TX, (Z)-hexadec-13-en-11-yn-1-yl acetate (IUPAC name) (438)+TX,(Z)-icos-13-en-10-one (IUPAC name) (448)+TX, (Z)-tetradec-7-en-1-al(IUPAC name) (782)+TX, (Z)-tetradec-9-en-1-ol (IUPAC name) (783)+TX,(Z)-tetradec-9-en-1-yl acetate (IUPAC name) (784)+TX,(7E,9Z)-dodeca-7,9-dien-1-yl acetate (IUPAC name) (283)+TX,(9Z,11E)-tetradeca-9,11-dien-1-yl acetate (IUPAC name) (780)+TX,(9Z,12E)-tetradeca-9,12-dien-1-yl acetate (IUPAC name) (781)+TX,14-methyloctadec-1-ene (IUPAC name) (545)+TX, 4-methylnonan-5-ol with4-methylnonan-5-one (IUPAC name) (544)+TX, alpha-multistriatin(alternative name) [CCN]+TX, brevicomin (alternative name) [CCN]+TX,codlelure (alternative name) [CCN]+TX, codlemone (alternative name)(167)+TX, cuelure (alternative name) (179)+TX, disparlure (277)+TX,dodec-8-en-1-yl acetate (IUPAC name) (286)+TX, dodec-9-en-1-yl acetate(IUPAC name) (287)+TX, dodeca-8+TX, 10-dien-1-yl acetate (IUPAC name)(284)+TX, dominicalure (alternative name) [CCN]+TX, ethyl4-methyloctanoate (IUPAC name) (317)+TX, eugenol (alternative name)[CCN]+TX, frontalin (alternative name) [CCN]+TX, gossyplure (alternativename) (420)+TX, grandlure (421)+TX, grandlure I (alternative name)(421)+TX, grandlure II (alternative name) (421)+TX, grandlure III(alternative name) (421)+TX, grandlure IV (alternative name) (421)+TX,hexalure [CCN]+TX, ipsdienol (alternative name) [CCN]+TX, ipsenol(alternative name) [CCN]+TX, japonilure (alternative name) (481)+TX,lineatin (alternative name) [CCN]+TX, litlure (alternative name)[CCN]+TX, looplure (alternative name) [CCN]+TX, medlure [CCN]+TX,megatomoic acid (alternative name) [CCN]+TX, methyl eugenol (alternativename) (540)+TX, muscalure (563)+TX, octadeca-2,13-dien-1-yl acetate(IUPAC name) (588)+TX, octadeca-3,13-dien-1-yl acetate (IUPAC name)(589)+TX, orfralure (alternative name) [CCN]+TX, oryctalure (alternativename) (317)+TX, ostramone (alternative name) [CCN]+TX, siglure [CCN]+TX,sordidin (alternative name) (736)+TX, sulcatol (alternative name)[CCN]+TX, tetradec-11-en-1-yl acetate (IUPAC name) (785)+TX, trimedlure(839)+TX, trimedlure A (alternative name) (839)+TX, trimedlure B₁(alternative name) (839)+TX, trimedlure B₂ (alternative name) (839)+TX,trimedlure C (alternative name) (839) and trunc-call (alternative name)[CCN]+TX, an insect repellent selected from the group of substancesconsisting of 2-(octylthio)ethanol (IUPAC name) (591)+TX, butopyronoxyl(933)+TX, butoxy(polypropylene glycol) (936)+TX, dibutyl adipate (IUPACname) (1046)+TX, dibutyl phthalate (1047)+TX, dibutyl succinate (IUPACname) (1048)+TX, diethyltoluamide [CCN]+TX, dimethyl carbate [CCN]+TX,dimethyl phthalate [CCN]+TX, ethyl hexanediol (1137)+TX, hexamide[CCN]+TX, methoquin-butyl (1276)+TX, methylneodecanamide [CCN]+TX,oxamate [CCN] and picaridin [CCN]+TX,

an insecticide selected from the group of substances consisting of1-dichloro-1-nitroethane (IUPAC/Chemical Abstracts name) (1058)+TX,1,1-dichloro-2,2-bis(4-ethylphenyl)ethane (IUPAC name) (1056), +TX,1,2-dichloropropane (IUPAC/Chemical Abstracts name) (1062)+TX,1,2-dichloropropane with 1,3-dichloropropene (IUPAC name) (1063)+TX,1-bromo-2-chloroethane (IUPAC/Chemical Abstracts name) (916)+TX,2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate (IUPAC name)(1451)+TX, 2,2-dichlorovinyl 2-ethylsulphinylethyl methyl phosphate(IUPAC name) (1066)+TX, 2-(1,3-dithiolan-2-yl)phenyl dimethylcarbamate(IUPAC/Chemical Abstracts name) (1109)+TX, 2-(2-butoxyethoxy)ethylthiocyanate (IUPAC/Chemical Abstracts name) (935)+TX,2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methylcarbamate (IUPAC/ChemicalAbstracts name) (1084)+TX, 2-(4-chloro-3,5-xylyloxy)ethanol (IUPAC name)(986)+TX, 2-chlorovinyl diethyl phosphate (IUPAC name) (984)+TX,2-imidazolidone (IUPAC name) (1225)+TX, 2-isovalerylindan-1,3-dione(IUPAC name) (1246)+TX, 2-methyl(prop-2-ynyl)aminophenyl methylcarbamate(IUPAC name) (1284)+TX, 2-thiocyanatoethyl laurate (IUPAC name)(1433)+TX, 3-bromo-1-chloroprop-1-ene (IUPAC name) (917)+TX,3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate (IUPAC name) (1283)+TX,4-methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate (IUPAC name)(1285)+TX, 5,5-dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate (IUPACname) (1085)+TX, abamectin (1)+TX, acephate (2)+TX, acetamiprid (4)+TX,acethion (alternative name) [CCN]+TX, acetoprole [CCN]+TX, acrinathrin(9)+TX, acrylonitrile (IUPAC name) (861)+TX, alanycarb (15)+TX, aldicarb(16)+TX, aldoxycarb (863)+TX, aldrin (864)+TX, allethrin (17)+TX,allosamidin (alternative name) [CCN]+TX, allyxycarb (866)+TX,alpha-cypermethrin (202)+TX, alpha-ecdysone (alternative name) [CCN]+TX,aluminium phosphide (640)+TX, amidithion (870)+TX, amidothioate(872)+TX, aminocarb (873)+TX, amiton (875)+TX, amiton hydrogen oxalate(875)+TX, amitraz (24)+TX, anabasine (877)+TX, athidathion (883)+TX, AVI382 (compound code)+TX, AZ 60541 (compound code)+TX, azadirachtin(alternative name) (41)+TX, azamethiphos (42)+TX, azinphos-ethyl(44)+TX, azinphos-methyl (45)+TX, azothoate (889)+TX, Bacillusthuringiensis delta endotoxins (alternative name) (52)+TX, bariumhexafluorosilicate (alternative name) [CCN]+TX, barium polysulfide(IUPAC/Chemical Abstracts name) (892)+TX, barthrin [CCN]+TX, Bayer22/190 (development code) (893)+TX, Bayer 22408 (development code)(894)+TX, bendiocarb (58)+TX, benfuracarb (60)+TX, bensultap (66)+TX,beta-cyfluthrin (194)+TX, beta-cypermethrin (203)+TX, bifenthrin(76)+TX, bioallethrin (78)+TX, bioallethrin S-cyclopentenyl isomer(alternative name) (79)+TX, bioethanomethrin [CCN]+TX, biopermethrin(908)+TX, bioresmethrin (80)+TX, bis(2-chloroethyl) ether (IUPAC name)(909)+TX, bistrifluron (83)+TX, borax (86)+TX, brofenvalerate(alternative name)+TX, bromfenvinfos (914)+TX, bromocyclen (918)+TX,bromo-DDT (alternative name) [CCN]+TX, bromophos (920)+TX,bromophos-ethyl (921)+TX, bufencarb (924)+TX, buprofezin (99)+TX,butacarb (926)+TX, butathiofos (927)+TX, butocarboxim (103)+TX, butonate(932)+TX, butoxycarboxim (104)+TX, butylpyridaben (alternative name)+TX,cadusafos (109)+TX, calcium arsenate [CCN]+TX, calcium cyanide (444)+TX,calcium polysulfide (IUPAC name) (111)+TX, camphechlor (941)+TX,carbanolate (943)+TX, carbaryl (115)+TX, carbofuran (118)+TX, carbondisulfide (IUPAC/Chemical Abstracts name) (945)+TX, carbon tetrachloride(IUPAC name) (946)+TX, carbophenothion (947)+TX, carbosulfan (119)+TX,cartap (123)+TX, cartap hydrochloride (123)+TX, cevadine (alternativename) (725)+TX, chlorbicyclen (960)+TX, chlordane (128)+TX, chlordecone(963)+TX, chlordimeform (964)+TX, chlordimeform hydrochloride (964)+TX,chlorethoxyfos (129)+TX, chlorfenapyr (130)+TX, chlorfenvinphos(131)+TX, chlorfluazuron (132)+TX, chlormephos (136)+TX, chloroform[CCN]+TX, chloropicrin (141)+TX, chlorphoxim (989)+TX, chlorprazophos(990)+TX, chlorpyrifos (145)+TX, chlorpyrifos-methyl (146)+TX,chlorthiophos (994)+TX, chromafenozide (150)+TX, cinerin I (696)+TX,cinerin II (696)+TX, cinerins (696)+TX, cis-resmethrin (alternativename)+TX, cismethrin (80)+TX, clocythrin (alternative name)+TX,cloethocarb (999)+TX, closantel (alternative name) [CCN]+TX,clothianidin (165)+TX, copper acetoarsenite [CCN]+TX, copper arsenate[CCN]+TX, copper oleate [CCN]+TX, coumaphos (174)+TX, coumithoate(1006)+TX, crotamiton (alternative name) [CCN]+TX, crotoxyphos(1010)+TX, crufomate (1011)+TX, cryolite (alternative name) (177)+TX, CS708 (development code) (1012)+TX, cyanofenphos (1019)+TX, cyanophos(184)+TX, cyanthoate (1020)+TX, cyclethrin [CCN]+TX, cycloprothrin(188)+TX, cyfluthrin (193)+TX, cyhalothrin (196)+TX, cypermethrin(201)+TX, cyphenothrin (206)+TX, cyromazine (209)+TX, cythioate(alternative name) [CCN]+TX, d-limonene (alternative name) [CCN]+TX,d-tetramethrin (alternative name) (788)+TX, DAEP (1031)+TX, dazomet(216)+TX, DDT (219)+TX, decarbofuran (1034)+TX, deltamethrin (223)+TX,demephion (1037)+TX, demephion-O (1037)+TX, demephion-S (1037)+TX,demeton (1038)+TX, demeton-methyl (224)+TX, demeton-O (1038)+TX,demeton-O-methyl (224)+TX, demeton-S (1038)+TX, demeton-S-methyl(224)+TX, demeton-S-methylsulphon (1039)+TX, diafenthiuron (226)+TX,dialifos (1042)+TX, diamidafos (1044)+TX, diazinon (227)+TX, dicapthon(1050)+TX, dichlofenthion (1051)+TX, dichlorvos (236)+TX, dicliphos(alternative name)+TX, dicresyl (alternative name) [CCN]+TX, dicrotophos(243)+TX, dicyclanil (244)+TX, dieldrin (1070)+TX, diethyl5-methylpyrazol-3-yl phosphate (IUPAC name) (1076)+TX, diflubenzuron(250)+TX, dilor (alternative name) [CCN]+TX, dimefluthrin [CCN]+TX,dimefox (1081)+TX, dimetan (1085)+TX, dimethoate (262)+TX, dimethrin(1083)+TX, dimethylvinphos (265)+TX, dimetilan (1086)+TX, dinex(1089)+TX, dinex-diclexine (1089)+TX, dinoprop (1093)+TX, dinosam(1094)+TX, dinoseb (1095)+TX, dinotefuran (271)+TX, diofenolan(1099)+TX, dioxabenzofos (1100)+TX, dioxacarb (1101)+TX, dioxathion(1102)+TX, disulfoton (278)+TX, dithicrofos (1108)+TX, DNOC (282)+TX,doramectin (alternative name) [CCN]+TX, DSP (1115)+TX, ecdysterone(alternative name) [CCN]+TX, EI 1642 (development code) (1118)+TX,emamectin (291)+TX, emamectin benzoate (291)+TX, EMPC (1120)+TX,empenthrin (292)+TX, endosulfan (294)+TX, endothion (1121)+TX, endrin(1122)+TX, EPBP (1123)+TX, EPN (297)+TX, epofenonane (1124)+TX,eprinomectin (alternative name) [CCN]+TX, esfenvalerate (302)+TX,etaphos (alternative name) [CCN]+TX, ethiofencarb (308)+TX, ethion(309)+TX, ethiprole (310)+TX, ethoate-methyl (1134)+TX, ethoprophos(312)+TX, ethyl formate (IUPAC name) [CCN]+TX, ethyl-DDD (alternativename) (1056)+TX, ethylene dibromide (316)+TX, ethylene dichloride(chemical name) (1136)+TX, ethylene oxide [CCN]+TX, etofenprox (319)+TX,etrimfos (1142)+TX, EXD (1143)+TX, famphur (323)+TX, fenamiphos(326)+TX, fenazaflor (1147)+TX, fenchlorphos (1148)+TX, fenethacarb(1149)+TX, fenfluthrin (1150)+TX, fenitrothion (335)+TX, fenobucarb(336)+TX, fenoxacrim (1153)+TX, fenoxycarb (340)+TX, fenpirithrin(1155)+TX, fenpropathrin (342)+TX, fenpyrad (alternative name)+TX,fensulfothion (1158)+TX, fenthion (346)+TX, fenthion-ethyl [CCN]+TX,fenvalerate (349)+TX, fipronil (354)+TX, flonicamid (358)+TX,flubendiamide (CAS. Reg. No.: 272451-65-7)+TX, flucofuron (1168)+TX,flucycloxuron (366)+TX, flucythrinate (367)+TX, fluenetil (1169)+TX,flufenerim [CCN]+TX, flufenoxuron (370)+TX, flufenprox (1171)+TX,flumethrin (372)+TX, fluvalinate (1184)+TX, FMC 1137 (development code)(1185)+TX, fonofos (1191)+TX, formetanate (405)+TX, formetanatehydrochloride (405)+TX, formothion (1192)+TX, formparanate (1193)+TX,fosmethilan (1194)+TX, fospirate (1195)+TX, fosthiazate (408)+TX,fosthietan (1196)+TX, furathiocarb (412)+TX, furethrin (1200)+TX,gamma-cyhalothrin (197)+TX, gamma-HCH (430)+TX, guazatine (422)+TX,guazatine acetates (422)+TX, GY-81 (development code) (423)+TX,halfenprox (424)+TX, halofenozide (425)+TX, HCH (430)+TX, HEOD(1070)+TX, heptachlor (1211)+TX, heptenophos (432)+TX, heterophos[CCN]+TX, hexaflumuron (439)+TX, HHDN (864)+TX, hydramethylnon (443)+TX,hydrogen cyanide (444)+TX, hydroprene (445)+TX, hyquincarb (1223)+TX,imidacloprid (458)+TX, imiprothrin (460)+TX, indoxacarb (465)+TX,iodomethane (IUPAC name) (542)+TX, IPSP (1229)+TX, isazofos (1231)+TX,isobenzan (1232)+TX, isocarbophos (alternative name) (473)+TX, isodrin(1235)+TX, isofenphos (1236)+TX, isolane (1237)+TX, isoprocarb (472)+TX,isopropyl O-(methoxyaminothiophosphoryl)salicylate (IUPAC name)(473)+TX, isoprothiolane (474)+TX, isothioate (1244)+TX, isoxathion(480)+TX, ivermectin (alternative name) [CCN]+TX, jasmolin I (696)+TX,jasmolin II (696)+TX, jodfenphos (1248)+TX, juvenile hormone I(alternative name) [CCN]+TX, juvenile hormone II (alternative name)[CCN]+TX, juvenile hormone III (alternative name) [CCN]+TX, kelevan(1249)+TX, kinoprene (484)+TX, lambda-cyhalothrin (198)+TX, leadarsenate [CCN]+TX, lepimectin (CCN)+TX, leptophos (1250)+TX, lindane(430)+TX, lirimfos (1251)+TX, lufenuron (490)+TX, lythidathion(1253)+TX, m-cumenyl methylcarbamate (IUPAC name) (1014)+TX, magnesiumphosphide (IUPAC name) (640)+TX, malathion (492)+TX, malonoben(1254)+TX, mazidox (1255)+TX, mecarbam (502)+TX, mecarphon (1258)+TX,menazon (1260)+TX, mephosfolan (1261)+TX, mercurous chloride (513)+TX,mesulfenfos (1263)+TX, metaflumizone (CCN)+TX, metam (519)+TX,metam-potassium (alternative name) (519)+TX, metam-sodium (519)+TX,methacrifos (1266)+TX, methamidophos (527)+TX, methanesulphonyl fluoride(IUPAC/Chemical Abstracts name) (1268)+TX, methidathion (529)+TX,methiocarb (530)+TX, methocrotophos (1273)+TX, methomyl (531)+TX,methoprene (532)+TX, methoquin-butyl (1276)+TX, methothrin (alternativename) (533)+TX, methoxychlor (534)+TX, methoxyfenozide (535)+TX, methylbromide (537)+TX, methyl isothiocyanate (543)+TX, methylchloroform(alternative name) [CCN]+TX, methylene chloride [CCN]+TX, metofluthrin[CCN]+TX, metolcarb (550)+TX, metoxadiazone (1288)+TX, mevinphos(556)+TX, mexacarbate (1290)+TX, milbemectin (557)+TX, milbemycin oxime(alternative name) [CCN]+TX, mipafox (1293)+TX, mirex (1294)+TX,monocrotophos (561)+TX, morphothion (1300)+TX, moxidectin (alternativename) [CCN]+TX, naftalofos (alternative name) [CCN]+TX, naled (567)+TX,naphthalene (IUPAC/Chemical Abstracts name) (1303)+TX, NC-170(development code) (1306)+TX, NC-184 (compound code)+TX, nicotine(578)+TX, nicotine sulfate (578)+TX, nifluridide (1309)+TX, nitenpyram(579)+TX, nithiazine (1311)+TX, nitrilacarb (1313)+TX, nitrilacarb 1:1zinc chloride complex (1313)+TX, NNI-0101 (compound code)+TX, NNI-0250(compound code)+TX, nornicotine (traditional name) (1319)+TX, novaluron(585)+TX, noviflumuron (586)+TX, O-5-dichloro-4-iodophenyl O-ethylethylphosphonothioate (IUPAC name) (1057)+TX, O,O-diethylO-4-methyl-2-oxo-2H-chromen-7-ylphosphorothioate (IUPAC name) (1074)+TX,O,O-diethyl O-6-methyl-2-propylpyrimidin-4-ylphosphorothioate (IUPACname) (1075)+TX, O,O,O′,O′-tetrapropyl dithiopyrophosphate (IUPAC name)(1424)+TX, oleic acid (IUPAC name) (593)+TX, omethoate (594)+TX, oxamyl(602)+TX, oxydemeton-methyl (609)+TX, oxydeprofos (1324)+TX,oxydisulfoton (1325)+TX, pp′-DDT (219)+TX, para-dichlorobenzene[CCN]+TX, parathion (615)+TX, parathion-methyl (616)+TX, penfluron(alternative name) [CCN]+TX, pentachlorophenol (623)+TX,pentachlorophenyl laurate (IUPAC name) (623)+TX, permethrin (626)+TX,petroleum oils (alternative name) (628)+TX, PH 60-38 (development code)(1328)+TX, phenkapton (1330)+TX, phenothrin (630)+TX, phenthoate(631)+TX, phorate (636)+TX, phosalone (637)+TX, phosfolan (1338)+TX,phosmet (638)+TX, phosnichlor (1339)+TX, phosphamidon (639)+TX,phosphine (IUPAC name) (640)+TX, phoxim (642)+TX, phoxim-methyl(1340)+TX, pirimetaphos (1344)+TX, pirimicarb (651)+TX, pirimiphos-ethyl(1345)+TX, pirimiphos-methyl (652)+TX, polychlorodicyclopentadieneisomers (IUPAC name) (1346)+TX, polychloroterpenes (traditional name)(1347)+TX, potassium arsenite [CCN]+TX, potassium thiocyanate [CCN]+TX,prallethrin (655)+TX, precocene I (alternative name) [CCN]+TX, precoceneII (alternative name) [CCN]+TX, precocene III (alternative name)[CCN]+TX, primidophos (1349)+TX, profenofos (662)+TX, profluthrin[CCN]+TX, promacyl (1354)+TX, promecarb (1355)+TX, propaphos (1356)+TX,propetamphos (673)+TX, propoxur (678)+TX, prothidathion (1360)+TX,prothiofos (686)+TX, prothoate (1362)+TX, protrifenbute [CCN]+TX,pymetrozine (688)+TX, pyraclofos (689)+TX, pyrazophos (693)+TX,pyresmethrin (1367)+TX, pyrethrin I (696)+TX, pyrethrin II (696)+TX,pyrethrins (696)+TX, pyridaben (699)+TX, pyridalyl (700)+TX,pyridaphenthion (701)+TX, pyrimidifen (706)+TX, pyrimitate (1370)+TX,pyriproxyfen (708)+TX, quassia (alternative name) [CCN]+TX, quinalphos(711)+TX, quinalphos-methyl (1376)+TX, quinothion (1380)+TX, quintiofos(1381)+TX, R-1492 (development code) (1382)+TX, rafoxanide (alternativename) [CCN]+TX, resmethrin (719)+TX, rotenone (722)+TX, RU 15525(development code) (723)+TX, RU 25475 (development code) (1386)+TX,ryania (alternative name) (1387)+TX, ryanodine (traditional name)(1387)+TX, sabadilla (alternative name) (725)+TX, schradan (1389)+TX,sebufos (alternative name)+TX, selamectin (alternative name) [CCN]+TX,SI-0009 (compound code)+TX, SI-0205 (compound code)+TX, SI-0404(compound code)+TX, SI-0405 (compound code)+TX, silafluofen (728)+TX, SN72129 (development code) (1397)+TX, sodium arsenite [CCN]+TX, sodiumcyanide (444)+TX, sodium fluoride (IUPAC/Chemical Abstracts name)(1399)+TX, sodium hexafluorosilicate (1400)+TX, sodiumpentachlorophenoxide (623)+TX, sodium selenate (IUPAC name) (1401)+TX,sodium thiocyanate [CCN]+TX, sophamide (1402)+TX, spinosad (737)+TX,spiromesifen (739)+TX, spirotetrmat (CCN)+TX, sulcofuron (746)+TX,sulcofuron-sodium (746)+TX, sulfluramid (750)+TX, sulfotep (753)+TX,sulphuryl fluoride (756)+TX, sulprofos (1408)+TX, tar oils (alternativename) (758)+TX, tau-fluvalinate (398)+TX, tazimcarb (1412)+TX, TDE(1414)+TX, tebufenozide (762)+TX, tebufenpyrad (763)+TX, tebupirimfos(764)+TX, teflubenzuron (768)+TX, tefluthrin (769)+TX, temephos(770)+TX, TEPP (1417)+TX, terallethrin (1418)+TX, terbam (alternativename)+TX, terbufos (773)+TX, tetrachloroethane [CCN]+TX,tetrachlorvinphos (777)+TX, tetramethrin (787)+TX, theta-cypermethrin(204)+TX, thiacloprid (791)+TX, thiafenox (alternative name)+TX,thiamethoxam (792)+TX, thicrofos (1428)+TX, thiocarboxime (1431)+TX,thiocyclam (798)+TX, thiocyclam hydrogen oxalate (798)+TX, thiodicarb(799)+TX, thiofanox (800)+TX, thiometon (801)+TX, thionazin (1434)+TX,thiosultap (803)+TX, thiosultap-sodium (803)+TX, thuringiensin(alternative name) [CCN]+TX, tolfenpyrad (809)+TX, tralomethrin(812)+TX, transfluthrin (813)+TX, transpermethrin (1440)+TX, triamiphos(1441)+TX, triazamate (818)+TX, triazophos (820)+TX, triazuron(alternative name)+TX, trichlorfon (824)+TX, trichlormetaphos-3(alternative name) [CCN]+TX, trichloronat (1452)+TX, trifenofos(1455)+TX, triflumuron (835)+TX, trimethacarb (840)+TX, triprene(1459)+TX, vamidothion (847)+TX, vaniliprole [CCN]+TX, veratridine(alternative name) (725)+TX, veratrine (alternative name) (725)+TX, XMC(853)+TX, xylylcarb (854)+TX, YI-5302 (compound code)+TX,zeta-cypermethrin (205)+TX, zetamethrin (alternative name)+TX, zincphosphide (640)+TX, zolaprofos (1469) and ZXI 8901 (development code)(858)+TX, cyantraniliprole [736994-63-19]+TX, chlorantraniliprole[500008-45-7]+TX, cyenopyrafen [560121-52-0]+TX, cyflumetofen[400882-07-7]+TX, pyrifluquinazon [337458-27-2]+TX, spinetoram[187166-40-1+187166-15-0]+TX, spirotetramat [203313-25-1]+TX,sulfoxaflor [946578-00-3]+TX, flufiprole [704886-18-0]+TX, meperfluthrin[915288-13-0]+TX, tetramethylfluthrin [84937-88-2]+TX,

a molluscicide selected from the group of substances consisting ofbis(tributyltin) oxide (IUPAC name) (913)+TX, bromoacetamide [CCN]+TX,calcium arsenate [CCN]+TX, cloethocarb (999)+TX, copper acetoarsenite[CCN]+TX, copper sulfate (172)+TX, fentin (347)+TX, ferric phosphate(IUPAC name) (352)+TX, metaldehyde (518)+TX, methiocarb (530)+TX,niclosamide (576)+TX, niclosamide-olamine (576)+TX, pentachlorophenol(623)+TX, sodium pentachlorophenoxide (623)+TX, tazimcarb (1412)+TX,thiodicarb (799)+TX, tributyltin oxide (913)+TX, trifenmorph (1454)+TX,trimethacarb (840)+TX, triphenyltin acetate (IUPAC name) (347) andtriphenyltin hydroxide (IUPAC name) (347)+TX, pyriprole[394730-71-3]+TX, a nematicide selected from the group of substancesconsisting of AKD-3088 (compound code)+TX, 1,2-dibromo-3-chloropropane(IUPAC/Chemical Abstracts name) (1045)+TX, 1,2-dichloropropane(IUPAC/Chemical Abstracts name) (1062)+TX, 1,2-dichloropropane with1,3-dichloropropene (IUPAC name) (1063)+TX, 1,3-dichloropropene(233)+TX, 3,4-dichlorotetrahydrothiophene 1,1-dioxide (IUPAC/ChemicalAbstracts name) (1065)+TX, 3-(4-chlorophenyl)-5-methylrhodanine (IUPACname) (980)+TX, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid(IUPAC name) (1286)+TX, 6-isopentenylaminopurine (alternative name)(210)+TX, abamectin (1)+TX, acetoprole [CCN]+TX, alanycarb (15)+TX,aldicarb (16)+TX, aldoxycarb (863)+TX, AZ 60541 (compound code)+TX,benclothiaz [CCN]+TX, benomyl (62)+TX, butylpyridaben (alternativename)+TX, cadusafos (109)+TX, carbofuran (118)+TX, carbon disulfide(945)+TX, carbosulfan (119)+TX, chloropicrin (141)+TX, chlorpyrifos(145)+TX, cloethocarb (999)+TX, cytokinins (alternative name) (210)+TX,dazomet (216)+TX, DBCP (1045)+TX, DCIP (218)+TX, diamidafos (1044)+TX,dichlofenthion (1051)+TX, dicliphos (alternative name)+TX, dimethoate(262)+TX, doramectin (alternative name) [CCN]+TX, emamectin (291)+TX,emamectin benzoate (291)+TX, eprinomectin (alternative name) [CCN]+TX,ethoprophos (312)+TX, ethylene dibromide (316)+TX, fenamiphos (326)+TX,fenpyrad (alternative name)+TX, fensulfothion (1158)+TX, fosthiazate(408)+TX, fosthietan (1196)+TX, furfural (alternative name) [CCN]+TX,GY-81 (development code) (423)+TX, heterophos [CCN]+TX, iodomethane(IUPAC name) (542)+TX, isamidofos (1230)+TX, isazofos (1231)+TX,ivermectin (alternative name) [CCN]+TX, kinetin (alternative name)(210)+TX, mecarphon (1258)+TX, metam (519)+TX, metam-potassium(alternative name) (519)+TX, metam-sodium (519)+TX, methyl bromide(537)+TX, methyl isothiocyanate (543)+TX, milbemycin oxime (alternativename) [CCN]+TX, moxidectin (alternative name) [CCN]+TX, Myrotheciumverrucaria composition (alternative name) (565)+TX, NC-184 (compoundcode)+TX, oxamyl (602)+TX, phorate (636)+TX, phosphamidon (639)+TX,phosphocarb [CCN]+TX, sebufos (alternative name)+TX, selamectin(alternative name) [CCN]+TX, spinosad (737)+TX, terbam (alternativename)+TX, terbufos (773)+TX, tetrachlorothiophene (IUPAC/ChemicalAbstracts name) (1422)+TX, thiafenox (alternative name)+TX, thionazin(1434)+TX, triazophos (820)+TX, triazuron (alternative name)+TX,xylenols [CCN]+TX, YI-5302 (compound code) and zeatin (alternative name)(210)+TX, fluensulfone [318290-98-1]+TX,

a nitrification inhibitor selected from the group of substancesconsisting of potassium ethylxanthate [CCN] and nitrapyrin (580)+TX,

a plant activator selected from the group of substances consisting ofacibenzolar (6)+TX, acibenzolar-S-methyl (6)+TX, probenazole (658) andReynoutria sachalinensis extract (alternative name) (720)+TX,

a rodenticide selected from the group of substances consisting of2-isovalerylindan-1,3-dione (IUPAC name) (1246)+TX,4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748)+TX,alpha-chlorohydrin [CCN]+TX, aluminium phosphide (640)+TX, antu(880)+TX, arsenous oxide (882)+TX, barium carbonate (891)+TX,bisthiosemi (912)+TX, brodifacoum (89)+TX, bromadiolone (91)+TX,bromethalin (92)+TX, calcium cyanide (444)+TX, chloralose (127)+TX,chlorophacinone (140)+TX, cholecalciferol (alternative name) (850)+TX,coumachlor (1004)+TX, coumafuryl (1005)+TX, coumatetralyl (175)+TX,crimidine (1009)+TX, difenacoum (246)+TX, difethialone (249)+TX,diphacinone (273)+TX, ergocalciferol (301)+TX, flocoumafen (357)+TX,fluoroacetamide (379)+TX, flupropadine (1183)+TX, flupropadinehydrochloride (1183)+TX, gamma-HCH (430)+TX, HCH (430)+TX, hydrogencyanide (444)+TX, iodomethane (IUPAC name) (542)+TX, lindane (430)+TX,magnesium phosphide (IUPAC name) (640)+TX, methyl bromide (537)+TX,norbormide (1318)+TX, phosacetim (1336)+TX, phosphine (IUPAC name)(640)+TX, phosphorus [CCN]+TX, pindone (1341)+TX, potassium arsenite[CCN]+TX, pyrinuron (1371)+TX, scilliroside (1390)+TX, sodium arsenite[CCN]+TX, sodium cyanide (444)+TX, sodium fluoro-acetate (735)+TX,strychnine (745)+TX, thallium sulfate [CCN]+TX, warfarin (851) and zincphosphide (640)+TX,

a synergist selected from the group of substances consisting of2-(2-butoxyethoxy)ethyl piperonylate (IUPAC name) (934)+TX,5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (IUPAC name) (903)+TX,farnesol with nerolidol (alternative name) (324)+TX, MB-599 (developmentcode) (498)+TX, MGK 264 (development code) (296)+TX, piperonyl butoxide(649)+TX, piprotal (1343)+TX, propyl isomer (1358)+TX, 5421 (developmentcode) (724)+TX, sesamex (1393)+TX, sesasmolin (1394) and sulfoxide(1406)+TX,

an animal repellent selected from the group of substances consisting ofanthraquinone (32)+TX, chloralose (127)+TX, copper naphthenate [CCN]+TX,copper oxychloride (171)+TX, diazinon (227)+TX, dicyclopentadiene(chemical name) (1069)+TX, guazatine (422)+TX, guazatine acetates(422)+TX, methiocarb (530)+TX, pyridin-4-amine (IUPAC name) (23)+TX,thiram (804)+TX, trimethacarb (840)+TX, zinc naphthenate [CCN] and ziram(856)+TX,

a virucide selected from the group of substances consisting of imanin(alternative name) [CCN] and ribavirin (alternative name) [CCN]+TX,

a wound protectant selected from the group of substances consisting ofmercuric oxide (512)+TX, octhilinone (590) and thiophanate-methyl(802)+TX,

and biologically active compounds selected from the group consisting ofazaconazole (60207-31-0]+TX, bitertanol [70585-36-3]+TX, bromuconazole[116255-48-2]+TX, cyproconazole [94361-06-5]+TX, difenoconazole[119446-68-3]+TX, diniconazole [83657-24-3]+TX, epoxiconazole[106325-08-0]+TX, fenbuconazole [114369-43-6]+TX, fluquinconazole[136426-54-5]+TX, flusilazole [85509-19-9]+TX, flutriafol[76674-21-0]+TX, hexaconazole [79983-71-4]+TX, imazalil [35554-44-0]+TX,imibenconazole [86598-92-7]+TX, ipconazole [125225-28-7]+TX, metconazole[125116-23-6]+TX, myclobutanil [88671-89-0]+TX, pefurazoate[101903-30-4]+TX, penconazole [66246-88-6]+TX, prothioconazole[178928-70-6]+TX, pyrifenox [88283-41-4]+TX, prochloraz [67747-09-5]+TX,propiconazole [60207-90-1]+TX, simeconazole [149508-90-7]+TX,tebuconazole [107534-96-3]+TX, tetraconazole [112281-77-3]+TX,triadimefon [43121-43-3]+TX, triadimenol [55219-65-3]+TX, triflumizole[99387-89-0]+TX, triticonazole [131983-72-7]+TX, ancymidol[12771-68-5]+TX, fenarimol [60168-88-9]+TX, nuarimol [63284-71-9]+TX,bupirimate [41483-43-6]+TX, dimethirimol [5221-53-4]+TX, ethirimol[23947-60-6]+TX, dodemorph [1593-77-7]+TX, fenpropidine [67306-00-7]+TX,fenpropimorph [67564-91-4]+TX, spiroxamine [118134-30-8]+TX, tridemorph[81412-43-3]+TX, cyprodinil [121552-61-2]+TX, mepanipyrim[110235-47-7]+TX, pyrimethanil [53112-28-0]+TX, fenpiclonil[74738-17-3]+TX, fludioxonil [131341-86-1]+TX, benalaxyl[71626-11-4]+TX, furalaxyl [57646-30-7]+TX, metalaxyl [57837-19-1]+TX,R-metalaxyl [70630-17-0]+TX, ofurace [58810-48-3]+TX, oxadixyl[77732-09-3]+TX, benomyl [17804-35-2]+TX, carbendazim [10605-21-7]+TX,debacarb [62732-91-6]+TX, fuberidazole [3878-19-1]+TX, thiabendazole[148-79-8]+TX, chlozolinate [84332-86-5]+TX, dichlozoline[24201-58-9]+TX, iprodione [36734-19-7]+TX, myclozoline [54864-61-8]+TX,procymidone [32809-16-8]+TX, vinclozoline [50471-44-8]+TX, boscalid[188425-85-6]+TX, carboxin [5234-68-4]+TX, fenfuram [24691-80-3]+TX,flutolanil [66332-96-5]+TX, mepronil [55814-41-0]+TX, oxycarboxin[5259-88-1]+TX, penthiopyrad [183675-82-3]+TX, thifluzamide[130000-40-7]+TX, guazatine [108173-90-6]+TX, dodine [2439-10-3][112-65-2] (free base)+TX, iminoctadine [13516-27-3]+TX, azoxystrobin[131860-33-8]+TX, dimoxystrobin [149961-52-4]+TX, enestroburin {Proc.BCPC, Int. Congr., Glasgow, 2003, 1, 93}+TX, fluoxastrobin[361377-29-9]+TX, kresoxim-methyl [143390-89-0]+TX, metominostrobin[133408-50-1]+TX, trifloxystrobin [141517-21-7]+TX, orysastrobin[248593-16-0]+TX, picoxystrobin [117428-22-5]+TX, pyraclostrobin[175013-18-0]+TX, ferbam [14484-64-1]+TX, mancozeb [8018-01-7]+TX, maneb[12427-38-2]+TX, metiram [9006-42-2]+TX, propineb [12071-83-9]+TX,thiram [137-26-8]+TX, zineb [12122-67-7]+TX, ziram [137-30-4]+TX,captafol [2425-06-1]+TX, captan [133-06-2]+TX, dichlofluanid[1085-98-9]+TX, fluoroimide [41205-21-4]+TX, folpet [133-07-3]+TX,tolylfluanid [731-27-1]+TX, bordeaux mixture [8011-63-0]+TX,copperhydroxid [20427-59-2]+TX, copperoxychlorid [1332-40-7]+TX,coppersulfat [7758-98-7]+TX, copperoxid [1317-39-1]+TX, mancopper[53988-93-5]+TX, oxine-copper [10380-28-6]+TX, dinocap [131-72-6]+TX,nitrothal-isopropyl [10552-74-6]+TX, edifenphos [17109-49-8]+TX,iprobenphos [26087-47-8]+TX, isoprothiolane [50512-35-1]+TX, phosdiphen[36519-00-3]+TX, pyrazophos [13457-18-6]+TX, tolclofos-methyl[57018-04-9]+TX, acibenzolar-S-methyl [135158-54-2]+TX, anilazine[101-05-3]+TX, benthiavalicarb [413615-35-7]+TX, blasticidin-S[2079-00-7]+TX, chinomethionat [2439-01-2]+TX, chloroneb [2675-77-6]+TX,chlorothalonil [1897-45-6]+TX, cyflufenamid [180409-60-3]+TX, cymoxanil[57966-95-7]+TX, dichlone [117-80-6]+TX, diclocymet [139920-32-4]+TX,diclomezine [62865-36-5]+TX, dicloran [99-30-9]+TX, diethofencarb[87130-20-9]+TX, dimethomorph [110488-70-5]+TX, SYP-LI90 (Flumorph)[211867-47-9]+TX, dithianon [3347-22-6]+TX, ethaboxam [162650-77-3]+TX,etridiazole [2593-15-9]+TX, famoxadone [131807-57-3]+TX, fenamidone[161326-34-7]+TX, fenoxanil [115852-48-7]+TX, fentin [668-34-8]+TX,ferimzone [89269-64-7]+TX, fluazinam [79622-59-6]+TX, fluopicolide[239110-15-7]+TX, flusulfamide [106917-52-6]+TX, fenhexamid[126833-17-8]+TX, fosetyl-aluminium [39148-24-8]+TX, hymexazol[10004-44-1]+TX, iprovalicarb [140923-17-7]+TX, IKF-916 (Cyazofamid)[120116-88-3]+TX, kasugamycin [6980-18-3]+TX, methasulfocarb[66952-49-6]+TX, metrafenone [220899-03-6]+TX, pencycuron[66063-05-6]+TX, phthalide [27355-22-2]+TX, polyoxins [11113-80-7]+TX,probenazole [27605-76-1]+TX, propamocarb [25606-41-1]+TX, proquinazid[189278-12-4]+TX, pyroquilon [57369-32-1]+TX, quinoxyfen[124495-18-7]+TX, quintozene [82-68-8]+TX, sulphur [7704-34-9]+TX,tiadinil [223580-51-6]+TX, triazoxide [72459-58-6]+TX, tricyclazole[41814-78-2]+TX, triforine [26644-46-2]+TX, validamycin [37248-47-8]+TX,zoxamide (RH7281) [156052-68-5]+TX, mandipropamid [374726-62-2]+TX,isopyrazam [881685-58-1]+TX, sedaxane [874967-67-6]+TX,3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid(9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl)-amide(disclosed in WO 2007/048556)+TX,3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid[2-(2,4-dichlorophenyl)-2-methoxy-1-methyl-ethyl]-amide (disclosed in WO2008/148570)+TX,1-[4-[4-[(5S)5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone+TX,1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone[1003318-67-9], both disclosed in WO 2010/123791, WO 2008/013925, WO2008/013622 and WO 2011/051243 page 20)+TX,3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid(3′,4′,5′-trifluoro-biphenyl-2-yl)-amide (disclosed in WO 2006/087343)+TX, and 1-methyl-2-(2,4,5-trichloro-thiophen-3-yl)-ethyl]+TX.

The references in brackets behind the active ingredients, e.g.[3878-19-1] refer to the Chemical Abstracts Registry number. The abovedescribed mixing partners are known. Where the active ingredients areincluded in “The Pesticide Manual” [The Pesticide Manual—A WorldCompendium; Thirteenth Edition; Editor: C. D. S. TomLin; The BritishCrop Protection Council], they are described therein under the entrynumber given in round brackets hereinabove for the particular compound;for example, the compound “abamectin” is described under entry number(1). Where “[CCN]” is added hereinabove to the particular compound, thecompound in question is included in the “Compendium of Pesticide CommonNames”, which is accessible on the internet [A. Wood; Compendium ofPesticide Common Names, Copyright © 1995-2004]; for example, thecompound “acetoprole” is described under the internet addresshttp://www.alanwood.net/pesticides/acetoprole.html.

Most of the active ingredients described above are referred tohereinabove by a so-called “common name”, the relevant “ISO common name”or another “common name” being used in individual cases. If thedesignation is not a “common name”, the nature of the designation usedinstead is given in round brackets for the particular compound; in thatcase, the IUPAC name, the IUPAC/Chemical Abstracts name, a “chemicalname”, a “traditional name”, a “compound name” or a “development code”is used or, if neither one of those designations nor a “common name” isused, an “alternative name” is employed. “CAS Reg. No” means theChemical Abstracts Registry Number.

The active ingredient mixture of the compounds of formula I or onespecific compound selected from the Table A1 to A12 and Table B, and anactive ingredient as described above preferably in a mixing ratio offrom 100:1 to 1:6000, especially from 50:1 to 1:50, more especially in aratio of from 20:1 to 1:20, even more especially from 10:1 to 1:10, veryespecially from 5:1 and 1:5, special preference being given to a ratioof from 2:1 to 1:2, and a ratio of from 4:1 to 2:1 being likewisepreferred, above all in a ratio of 1:1, or 5:1, or 5:2, or 5:3, or 5:4,or 4:1, or 4:2, or 4:3, or 3:1, or 3:2, or 2:1, or 1:5, or 2:5, or 3:5,or 4:5, or 1:4, or 2:4, or 3:4, or 1:3, or 2:3, or 1:2, or 1:600, or1:300, or 1:150, or 1:35, or 2:35, or 4:35, or 1:75, or 2:75, or 4:75,or 1:6000, or 1:3000, or 1:1500, or 1:350, or 2:350, or 4:350, or 1:750,or 2:750, or 4:750. Those mixing ratios are understood to include, onthe one hand, ratios by weight and also, on the other hand, molarratios.

The mixtures as described above can be used in a method for controllingpests, which comprises applying a composition comprising a mixture asdescribed above to the pests or their environment, with the exception ofa method for treatment of the human or animal body by surgery or therapyand diagnostic methods practised on the human or animal body.

The mixtures comprising a compound of formula I or one specific onespecific compound selected from the Table A1 to A12 and Table B and oneor more active ingredients as described above can be applied, forexample, in a single “ready-mix” form, in a combined spray mixturecomposed from separate formulations of the single active ingredientcomponents, such as a “tank-mix”, and in a combined use of the singleactive ingredients when applied in a sequential manner, i.e. one afterthe other with a reasonably short period, such as a few hours or days.The order of applying the compounds of formula I or one specificcompound selected from the Table A1 (compounds A1.1 to A1.112) or aspecific one specific compound selected from the Table A1 to A12 andTable B, and the active ingredients as described above is not essentialfor working the present invention.

The compositions can also comprise further solid or liquid auxiliaries,such as stabilizers, for example unepoxidized or epoxidized vegetableoils (for example epoxidized coconut oil, rapeseed oil or soya oil),antifoams, for example silicone oil, preservatives, viscosityregulators, binders and/or tackifiers, fertilizers or other activeingredients for achieving specific effects, for example bactericides,fungicides, nematocides, plant activators, molluscicides or herbicides.

The compositions according to the invention are prepared in a mannerknown per se, in the absence of auxiliaries for example by grinding,screening and/or compressing a solid active ingredient and in thepresence of at least one auxiliary for example by intimately mixingand/or grinding the active ingredient with the auxiliary (auxiliaries).These processes for the preparation of the compositions and the use ofthe compounds I for the preparation of these compositions are also asubject of the invention.

The application methods for the compositions, that is the methods ofcontrolling pests of the abovementioned type, such as spraying,atomizing, dusting, brushing on, dressing, scattering or pouring—whichare to be selected to suit the intended aims of the prevailingcircumstances—and the use of the compositions for controlling pests ofthe abovementioned type are other subjects of the invention. Typicalrates of concentration are between 0.1 and 1000 ppm, preferably between0.1 and 500 ppm, of active ingredient. The rate of application perhectare is generally 1 to 2000 g of active ingredient per hectare, inparticular 10 to 1000 g/ha, preferably 10 to 600 g/ha.

A preferred method of application in the field of crop protection isapplication to the foliage of the plants (foliar application), it beingpossible to select frequency and rate of application to match the dangerof infestation with the pest in question. Alternatively, the activeingredient can reach the plants via the root system (systemic action),by drenching the locus of the plants with a liquid composition or byincorporating the active ingredient in solid form into the locus of theplants, for example into the soil, for example in the form of granules(soil application). In the case of paddy rice crops, such granules canbe metered into the flooded paddy-field.

The compositions according to the invention are also suitable for theprotection of plant propagation material, for example seeds, such asfruit, tubers or kernels, or nursery plants, against pests of theabovementioned type. The propagation material can be treated with thecompositions prior to planting, for example seed can be treated prior tosowing. Alternatively, the compositions can be applied to seed kernels(coating), either by soaking the kernels in a liquid composition or byapplying a layer of a solid composition. It is also possible to applythe compositions when the propagation material is planted to the site ofapplication, for example into the seed furrow during drilling. Thesetreatment methods for plant propagation material and the plantpropagation material thus treated are further subjects of the invention.

The compounds of formula (I) according to the invention can also be usedin combination with safeners. Preferably, in these mixtures, thecompound of the formula (I) or one specific compound selected from theTable A1 to A12 and Table B. The following mixtures with safeners,especially, come into consideration:

compound of formula (I)+cloquintocet-mexyl, compound of formula(I)+cloquintocet acid and salts thereof, compound of formula(I)+fenchlorazole-ethyl, compound of formula (I)+fenchlorazole acid andsalts thereof, compound of formula (I)+mefenpyr-diethyl, compound offormula (I)+mefenpyr diacid, compound of formula (I)+isoxadifen-ethyl,compound of formula (I)+isoxadifen acid, compound of formula(I)+furilazole, compound of formula (I)+furilazole R isomer, compound offormula (I)+benoxacor, compound of formula (I)+dichlormid, compound offormula (I)+AD-67, compound of formula (I)+oxabetrinil, compound offormula (I)+cyometrinil, compound of formula (I)+cyometrinil Z-isomer,compound of formula (I)+fenclorim, compound of formula(I)+cyprosulfamide, compound of formula (I)+naphthalic anhydride,compound of formula (I)+flurazole, compound of formula(I)+N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide,compound of formula (I)+CL 304,415, compound of formula (I)+dicyclonon,compound of formula (I)+fluxofenim, compound of formula (I)+DKA-24,compound of formula (I)+R-29148 and compound of formula (I)+PPG-1292. Asafening effect can also be observed for the mixtures compound of theformula (I)+dymron, compound of the formula (I)+MCPA, compound of theformula (I)+mecoprop and compound of the formula (I)+mecoprop-P.

The mixing partners of the TX may also be in the form of esters orsalts, as mentioned e.g. in The Pesticide Manual, 12th Edition (BCPC),2000.

In the above different lists of active ingredients to be mixed with aTX, the compound of the formula I is preferably one specific compoundselected from the Table A1 to A12 and Table B

In the above-mentioned mixtures of compounds of formula I, in particularone specific or one specific compound selected from the Table A1 to A12and Table B with other insecticides, fungicides, herbicides, safeners,adjuvants and the like, the mixing ratios can vary over a large rangeand are, preferably 100:1 to 1:6000, especially 50:1 to 1:50, moreespecially 20:1 to 1:20, even more especially 10:1 to 1:10. Those mixingratios are understood to include, on the one hand, ratios by weight andalso, on the other hand, molar ratios.

The mixtures can advantageously be used in the above-mentionedformulations (in which case “active ingredient” relates to therespective mixture of TX with the mixing partner).

Some mixtures may comprise active ingredients which have significantlydifferent physical, chemical or biological properties such that they donot easily lend themselves to the same conventional formulation type. Inthese circumstances other formulation types may be prepared. Forexample, where one active ingredient is a water insoluble solid and theother a water insoluble liquid, it may nevertheless be possible todisperse each active ingredient in the same continuous aqueous phase bydispersing the solid active ingredient as a suspension (using apreparation analogous to that of an SC) but dispersing the liquid activeingredient as an emulsion (using a preparation analogous to that of anEW). The resultant composition is a suspoemulsion (SE) formulation.

The mixtures comprising a TX one specific or one specific compoundselected from the Table A1 to A12 and Table B and one or more activeingredients as described above can be applied, for example, in a single“ready-mix” form, in a combined spray mixture composed from separateformulations of the single active ingredient components, such as a“tank-mix”, and in a combined use of the single active ingredients whenapplied in a sequential manner, i.e. one after the other with areasonably short period, such as a few hours or days. The order ofapplying the compounds of formula I or one specific or one specificcompound selected from the Table A1 to A12 and Table B and the activeingredients as described above is not essential for working the presentinvention.

The compounds of formula (I) may be mixed with soil, peat or otherrooting media for the protection of plants against seed-borne,soil-borne or foliar fungal diseases.

Examples of suitable synergists for use in the compositions includepiperonyl butoxide, sesamex, safroxan and dodecyl imidazole.

Suitable herbicides and plant-growth regulators for inclusion in thecompositions will depend upon the intended target and the effectrequired.

An example of a rice selective herbicide which may be included ispropanil. An example of a plant growth regulator for use in cotton isPIX™.

Some mixtures may comprise active ingredients which have significantlydifferent physical, chemical or biological properties such that they donot easily lend themselves to the same conventional formulation type. Inthese circumstances other formulation types may be prepared. Forexample, where one active ingredient is a water insoluble solid and theother a water insoluble liquid, it may nevertheless be possible todisperse each active ingredient in the same continuous aqueous phase bydispersing the solid active ingredient as a suspension (using apreparation analogous to that of an SC) but dispersing the liquid activeingredient as an emulsion (using a preparation analogous to that of anEW). The resultant composition is a suspoemulsion (SE) formulation.

The following Examples illustrate, but do not limit, the invention.

The compounds of the invention can be distinguished from known compoundsby virtue of greater efficacy at low application rates, which can beverified by the person skilled in the art using the experimentalprocedures outlined in the Examples, using lower application rates ifnecessary, for example 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm or 0.8ppm.

PREPARATION EXAMPLES Example P.1:N-[3-[[2-bromo-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-fluoro-phenyl]-N-ethyl-pyridine-4-carboxamide(Entry 2 of the table B) Step 1:N-[2-bromo-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-2-fluoro-3-nitro-benzamide

To a suspension of 11 g 2-fluoro-3-nitro-benzoic acid in 170 mldichloromethane a drop of N,N-dimethylformamide was added, followed by5.55 ml oxalyl dichloride. The resulting yellow suspension was stirredat ambient temperature for 5.5 hours. Then the solution was evaporatedto give 12.2 g of 2-fluoro-3-nitro-benzoyl chloride. To a solution of20.7 g2-bromo-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]anilinein 200 ml acetonitrile were added 12.2 g 2-fluoro-3-nitro-benzoylchloride and 0.84 g potassium iodide, and the resulting solution washeated to reflux for 18 hours. Then the solvent was evaporated, theresidue dissolved in ethyl acetate and extracted with aqueous sodiumbicarbonate. The organic phase was dried over anhydrous sodium sulfate,and the solvent was evaporated. Thus, 29 g of crudeN-[2-bromo-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-2-fluoro-3-nitro-benzamidewas obtained, which was used for step 2 without further purification. ¹HNMR (400 MHz, CDCl₃, δ in ppm): 8.44 (t, 1H), 8.28 (t, 1H), 8.07 (d,1H), 7.81 (s, 1H), 7.52 (m, 2H), 6.60 (t, 1H).

Step 2:3-amino-N-[2-bromo-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-2-fluoro-benzamide

To a suspension of 15.07 gN-[2-bromo-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-2-fluoro-3-nitro-benzamideand 3.67 g iron powder in 100 ml ethanol and 30 ml water was added 1 mlof concentrated hydrochloric acid. The resulting dark suspension washeated to reflux for 7 hours. The mixture was allowed to cool to ambienttemperature, filtered over celite, and the solvent was evaporated. Theresidue was dissolved in ethyl acetate and washed with brine. Theorganic phase was separated, dried over anhydrous sodium sulfate andevaporated. The residue was purified by chromatography on silica gel,using heptane/ethyl acetate (9:1 to 1:1) as eluent. Thus, 5.23 g of3-amino-N-[2-bromo-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-2-fluoro-benzamidewas obtained. ¹H NMR (400 MHz, CDCl₃, δ in ppm): 8.13 (d, 1H), 7.80 (s,1H), 7.52 (s, 1H), 7.45 (t, 1H), 7.11 (t, 1H), 6.99 (t, 1H), 6.60 (t,1H), 3.90 (s, broad, 2H).

Step 3:N-[2-bromo-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-3-(ethylamino)-2-fluoro-benzamide

To a solution of 2.32 g3-amino-N-[2-bromo-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-2-fluoro-benzamide,0.27 ml acetic acid and 0.20 g acetaldehyde in 19.2 ml methanol wasadded 311 mg sodium cyanoborohydride. The reaction mixture was stirredat ambient temperature for 2 hours. Then the solvent was evaporated andthe residue purified by chromatography on silica gel, using ethalacetate/heptane (1:19 to 1:4) as eluent. Thus, 1.98 g ofN-[2-bromo-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-3-(ethylamino)-2-fluoro-benzamidewas obtained. ¹H NMR (400 MHz, CDCl₃, δ in ppm): 8.12 (d, 1H), 7.79 (s,1H), 7.50 (s, 1H), 7.34 (t, 1H), 7.15 (t, 1H), 6.90 (t, 1H), 6.60 (t,1H), 3.98 (s, broad, 1H), 3.23 (q, 2H), 1.32 (t, 3H).

Step 4:N-[3-[[2-bromo-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-fluoro-phenyl]-N-ethyl-pyridine-4-carboxamide(Entry 2 of the table B)

To a solution of 0.70 gN-[2-bromo-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-3-(ethylamino)-2-fluoro-benzamidein 4.9 ml tetrahydrofuran was added 267 mg of isonicotinoyl chloridehydrochloride. The suspension was heated to 70° C. for 1 hour. Then thereaction mixture was allowed to ambient temperature, and the solvent wasevaporated. The residue was purified by chromatography on silica gel,using dichloromethane/methanol (1.5 to 4% methanol) as eluent. Thus, 765mgN-[3-[[2-bromo-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-fluoro-phenyl]-N-ethyl-pyridine-4-carboxamidewas obtained as a solid, mp=186-188° C. ¹H NMR (400 MHz, CDCl₃, δ inppm): 8.50 (s, broad, 2H), 8.02 (t, 1H), 7.83 (d, 1H), 7.78 (s, 1H),7.49 (s, 1H), 7.43 (t, 1H), 7.28 (t, 1H), 7.18 (s, broad, 2H), 6.55 (t,1H), 4.00 (m, broad, 2H), 1.28 (t, broad, 3H).

Example P.2:N-[3-[[2-bromo-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-fluoro-phenyl]-N-ethyl-1-oxido-pyridin-1-ium-4-carboxamide(Entry 11 of the table B)

To a solution of 454 mgN-[3-[[2-bromo-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-fluoro-phenyl]-N-ethyl-pyridine-4-carboxamidein 6.7 ml dichloromethane was added 173 mg 3-chlorobenzenecarboperoxoicacid. The resulting clear solution was stirred at ambient temperaturefor 18 hours. Then the solvent was evaporated, and the residue purifiedby chromatography on silica gel, using dichloromethane/methanol (1.5 to10% methanol) as eluent. Thus, 421 mgN-[3-[[2-bromo-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-fluoro-phenyl]-N-ethyl-1-oxido-pyridin-1-ium-4-carboxamidewas obtained as a solid, mp=103-106° C. ¹H NMR (400 MHz, CDCl₃, δ inppm): 8.07 (t, 1H), 8.01 (d, 2H), 7.88 (d, 1H), 7.80 (s, 1H), 7.50 (s,1H), 7.45 (t, 1H), 7.36 (t, 1H), 7.21 (d, 2H), 6.60 (t, 1H), 3.95 (m,broad, 2H), 1.27 (t, 3H).

Example P.3:N-[2-chloro-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-3-[(4-cyanobenzoyl)amino]-2-methoxy-benzamide(Entry 14 of the table B) Step 1:N-[2-chloro-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-2-fluoro-3-nitro-benzamide

12.3 g 2-fluoro-3-nitro-benzoic acid was dissolved in 3 mldichloromethane and a drop of N,N-dimethylformamide was added. Then 6.2ml oxalyl dichloride was added slowly over 30 min, and the mixture wasstirred at ambient temperature for 3.5 hours, then the solvent wasevaporated. The residue was dissolved in 70 ml of acetonitrile and addedslowly to a solution of 20 g2-chloro-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]anilineand of 0.92 g potassium iodide in 150 mL of acetonitrile. The reactionmixture was heated to reflux for 18 hours, allowed to cool to ambienttemperature, and the solvent evaporated. The residue was taken up inethyl acetate and washed with saturated aqueous sodium bicarbonate, theorganic phase was separated, dried over anhydrous sodium sulfate andevaporated. Thus, 31.5 g of crudeN-[2-chloro-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-2-fluoro-3-nitro-benzamidewas obtained, which was used for step 2 without further purification. ¹HNMR (400 MHz, CDCl₃, δ in ppm): 8.43 (t, 1H), 8.28 (t, 1H), 8.10 (d,1H), 7.67 (s, 1H), 7.50 (m, 2H), 6.60 (t, 1H).

Step 2:N-[2-chloro-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluorophenyl)ethyl]phenyl]-2-methoxy-3-nitro-benzamide

11.1 g ofN-[2-chloro-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-2-fluoro-3-nitro-benzamidewas dissolved in 190 ml methanol and 5.86 g of potassium carbonate wasadded. The mixture was heated to 50° C. for 3 hours. Then the solventwas evaporated, the residue was extracted with dichloromethane and waterand the layers separated. The organic layer was dried over anhydroussodium sulfate and the solvent evaporated. Thus, 11.04 g of crudeN-[2-chloro-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-2-methoxy-3-nitro-benzamidewas obtained, which was used for step 3 without further purification. ¹HNMR (400 MHz, CDCl₃, δ in ppm): 9.12 (s, 1H), 8.38 (d, 1H), 8.05 (d,1H), 7.65 (s, 1H), 7.45 (s, 1H), 7.43 (t, 1H), 6.61 (t, 1H), 4.14 (s,3H).

Step 3:3-amino-N-[2-chloro-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-2-methoxy-benzamide

To a solution of 11.04 gN-[2-chloro-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-2-methoxy-3-nitro-benzamidein 200 ml ethanol was added 40 ml of water, followed by 0.77 mlconcentrated hydrochloric acid and 2.85 g iron powder. The mixture washeated to reflux for 18 hours, then allowed to cool to ambienttemperature, filtered over celite, and the solvent was evaporated. Thus,10.06 g of3-amino-N-[2-chloro-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-2-methoxy-benzamidewas obtained, which was used for step 4 without further purification. ¹HNMR (400 MHz, CDCl₃, δ in ppm): 9.46 (s, 1H), 7.62 (s, 1H), 7.50 (d,1H), 7.45 (s, 1H), 7.10 (t, 1H), 6.97 (d, 1H), 6.61 (t, 1H), 3.98 (s,3H), 3.93 (s, broad, 2H).

Step 4:N-[2-chloro-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-3-[(4-cyanobenzoyl)amino]-2-methoxy-benzamide(Entry 14 of the table B)

To a solution of 123 mg3-amino-N-[2-chloro-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-2-methoxy-benzamidein 2.4 ml acetonitrile were added 4 mg of potassium iodide and 48 mg of4-cyanobenzoyl chloride. The mixture was heated to reflux for 3 hours,then allowed to cool to ambient temperature, and the solvent evaporated.The residue was dissolved in dichloromethane, washed with saturatedaqueous sodium sulfite, then with aqueous sodium bicarbonate, then withbrine. The organic phase was dried over anhydrous sodium sulfate, andthe solvent evaporated. Thus, without any further purification, 132 mgofN-[2-chloro-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-3-[(4-cyanobenzoyl)amino]-2-methoxy-benzamidewas obtained as a solid, mp=90-100° C. ¹H NMR (400 MHz, CDCl₃, δ inppm): 8.96 (s, 1H), 8.63 (d, 1H), 8.50 (s, 1H), 8.02 (d, 2H), 7.85 (m,3H), 7.64 (s, 1H), 7.46 (s, 1H), 7.37 (t, 1H), 6.63 (t, 1H), 4.03 (s,3H).

Example P.4:N-[3-[[2-bromo-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-methoxy-phenyl]-N-methyl-1-oxido-pyridin-1-ium-4-carboxamide(Entry 183 of the table B) Step 1:N-[2-bromo-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]acetamide

To a solution of2-bromo-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1(trifluoromethyl)ethyl]aniline (1.0 g) in acetic anhydride (5.5 ml) were added a fewdrops of concentrated sulfuric acid. The resulting solution was heatedat 60° C. for 200 minutes. The consumption of the starting aniline wasfollowed by LC-MS analysis of a aliquots of the reaction mixture. Thesolution was poured on an ice-water mixture and the resulting emulsionwas extracted with ethyl acetate. The combined organic layers were driedover sodium sulfate and evaporated under reduced pressure. The crudesolid was dissolved in tetrahydrofurane and treated with 30% (w/w)aqueous sodium hydroxide and stirred at 20° C. for 30 minutes. Thehydrolysis of the acetamide (side product of the reaction) to theacetamide was followed by LC-MS analysis of aliquots of the reactionmixture. The emulsion was extracted with ethyl acetate and the organicphase was dried over sodium sulfate. After evaporation of the solvent,the crude product was purified by chromatography through silica gelusing an eluent gradient (100% heptane to 40% ethyl acetate-60% heptane.After evaporation of the solvent the desired product was obtained. ¹HNMR (400 MHz, CDCl₃, δ in ppm): 7.75 (s, 1H), 7.46 (s, 1H), 6.90 (s,1H), 6.54 (t, J=68 Hz, 1H), 2.25 (s, 3H).

Step 2:N-[3-[acetyl-[2-bromo-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-methoxy-phenyl]-N-methyl-pyridine-4-carboxamide

To a solution ofN-[2-bromo-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]acetamide (0.76 g) in 1,2-dichloroethane (5.1 ml), at 0°C., was added triethylamine (0.60 g), followed by 0.52 g of2-methoxy-3-[methyl(pyridine-4-carbonyl)amino]benzoyl chloride (preparedfrom 2-methoxy-3-[methyl(pyridine-4-carbonyl)amino]benzoic acid, oxalylchloride and a catalytic amount of dimethylformamide in1,2-dichloroethane). The reaction was complete after stirring of thesuspension for 15 hours at 20° C. (LC-MS analysis). The reaction mixturewas then evaporated, the residue dissolved in ethyl acetate and thissolution washed with an aqueous solution of sodium hydrogencarbonate.The organic phase was dried over sodium sulfate, evaporated and theresidue was chromatographed on silica gel using a gradient from 1%methyl alcohol in dichloromethane to 10% methyl alcohol indichloromethane. The desired compound was isolated as a solid showing amelting point of 78-81° C.

Step 3:N-[3-[[2-bromo-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-methoxy-phenyl]-N-methyl-pyridine-4-carboxamide(Entry 182 of the table B)

To a solution ofN-[3-[acetyl-[2-bromo-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-methoxy-phenyl]-N-methyl-pyridine-4-carboxamide(0.278 g) in tetrahydrofurane (1.7 g) was added aqueous sodium hydroxide(1 M, 1.55 ml) and the resulting emulsion was stirred for 1.5 hour at20° C. The conversion was followed by LC-MS analysis. The reactionmixture was partitioned between water and ethyl acetate. The organicphase was dried over sodium sulfate and evaporated to yield the desiredcompound as a solid melting at 73-77° C. It was used without furtherpurification in the next step.

Step 4:N-[3-[[2-bromo-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-methoxy-phenyl]-N-methyl-1-oxido-pyridin-1-ium-4-carboxamide(Entry 183 of the table B)

A solution ofN-[3-[[2-bromo-6-(difluoromethoxy)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-methoxy-phenyl]-N-methyl-pyridine-4-carboxamide(0.145 g) in dichloromethane (1.70 g) was treated with 0.052 g of 75%meta-chloroperbenzoic acid. After 5 hours stirring at 20° C., fullconversion was observed by LC-MS and TLC analyses. The reaction mixturewas concentrated and submitted to column chromatography over silica gel,using a gradient from 1% methyl alcohol in dichloromethane to 7% methylalcohol in dichloromethane. ¹H NMR (400 MHz, CDCl₃, δ in ppm): 9.72(br.s, 1H), 8.08 (dd, 1H), 7.96 (br. ds, 2H), 7.76 (s, 1H), 7.56 (dd,1H), 7.45 (s, 1H), 7.40 (t, 1H), 7.20 (br. d, 2H), 6.60 (t, J=72 Hz,1H), 3.89 (s, 3H), 3.56 (s, 3H).

The compounds in tables B were prepared in the same or a similar way asdescribed above:

TABLE B [M + H] [M − H] Entry STRUCTURE RT (min) (measured) (measured)Method MP ° C. 1

200-204 2

186-188 3

192-196 4

78-82 5

1.88 672.27 UPLC1 121-124 6

1.94 684.3 UPLC1 121-126 7

119-124 8

220-999 9

1.97 712.31 UPLC1 85-90 10

2.12 700.03 UPLC2 86-89 11

103-106 12

112-116 13

1.15 626, 628 SQD13 14

1.93 640.32 UPLC1  90-100 15

1.06 604, 606 ZCQ13 16

1.08 616, 618 ZCQ13 17

2.12 656.07 UPLC2  95-100 18

105-110 19

183-184 20

 95-100 21

1.98 679.96 UPLC1 22

1.95 692.25 UPLC1 23

2.02 661.28 UPLC1 24

2.10 699.24 UPLC1 25

1.99 726.22 UPLC1 26

2.11 731.26 UPLC1 27

2.10 733.27 UPLC1 28

2.08 715.27 UPLC1 29

2.06 731.27 UPLC1 30

2.09 677.28 UPLC1 31

1.95 647.27 UPLC1 32

1.97 665.26 UPLC1 33

2.10 677.28 UPLC1 34

1.99 715.28 UPLC1 35

2.05 673.32 UPLC1 36

2.01 699.23 UPLC1 37

2.04 693.27 UPLC1 38

2.01 683.26 UPLC1 39

1.99 704.3 UPLC1 40

2.03 683.26 UPLC1 41

2.08 673.31 UPLC1 42

2.11 733.27 UPLC1 43

2.06 691.31 UPLC1 44

2.19 711.26 UPLC1 45

1.99 621.29 UPLC1 46

1.98 617.32 UPLC1 47

2.04 738.27 UPLC1 48

1.94 637.27 UPLC1 49

1.92 648.31 UPLC1 50

2.15 743.31 UPLC1 51

1.99 617.31 UPLC1 52

2.14 745.29 UPLC1 53

1.98 635.32 UPLC1 54

2.13 727.29 UPLC1 55

2.07 655.27 UPLC1 56

2.13 743.29 UPLC1 57

1.96 682.29 UPLC1 58

2.13 689.31 UPLC1 59

2.00 659.29 UPLC1 60

2.08 687.32 UPLC1 61

2.01 677.29 UPLC1 62

2.07 689.31 UPLC1 63

2.04 727.3 UPLC1 64

2.05 671.31 UPLC1 65

2.04 687.31 UPLC1 66

2.07 711.26 UPLC1 67

2.07 633.32 UPLC1 68

1.92 603.3 UPLC1 69

2.10 695.28 UPLC1 70

1.94 621.3 UPLC1 71

2.12 695.29 UPLC1 72

1.97 671.31 UPLC1 73

2.20 745.3 UPLC1 74

1.98 655.27 UPLC1 75

2.09 633.32 UPLC1 76

1.98 639.29 UPLC1 77

2.04 629.34 UPLC1 78

2.00 639.29 UPLC1 79

2.04 649.29 UPLC1 80

2.09 689.31 UPLC1 81

1.98 660.32 UPLC1 82

2.07 629.34 UPLC1 83

1.99 665.27 UPLC1 84

2.05 647.34 UPLC1 85

2.19 667.29 UPLC1 86

2.03 694.3 UPLC1 87

2.13 699.33 UPLC1 88

2.13 701.34 UPLC1 89

2.12 683.33 UPLC1 90

2.12 699.34 UPLC1 91

2.12 645.35 UPLC1 92

1.99 615.32 UPLC1 93

2.01 633.32 UPLC1 94

2.03 683.34 UPLC1 95

2.06 667.29 UPLC1 96

2.09 651.33 UPLC1 97

2.11 651.33 UPLC1 98

2.19 701.33 UPLC1 99

78-81 100

85-88 101

186-188 102

73-77 103

2.16 720.02 UPLC2 104

2.05 726.97 UPLC2 105

2.29 743.04 UPLC2 106

2.07 759.01 UPLC2 107

1.95 705.04 UPLC2 108

1.98 711 UPLC2 109

1.98 711 UPLC2 110

2.07 761 UPLC2 111

1.95 649.02 UPLC2 112

2.00 665.01 UPLC2 113

2.17 676.07 UPLC2 114

2.23 645.06 UPLC2 115

2.04 683.01 UPLC2 116

2.25 710.03 UPLC2 117

2.29 699.08 UPLC2 118

2.06 715.07 UPLC2 119

1.95 631.01 UPLC2 120

1.96 649.02 UPLC2 121

2.04 699.05 UPLC2 122

2.02 683 UPLC2 123

1.98 667.03 UPLC2 124

2.29 717.06 UPLC2 125

1.96 693.02 UPLC2 126

2.01 689.01 UPLC2 127

1.97 675.33 UPLC2 128

1.99 693.32 UPLC2 129

2.04 705.3 UPLC1 130

2.09 701.33 UPLC1 131

2.09 721.27 UPLC1 132

2.11 UPLC1 133

2.09 719.32 UPLC1 134

2.13 739.26 UPLC1 135

2.09 766.26 UPLC1 136

2.16 771.3 UPLC1 137

2.04 717.31 UPLC1 138

2.04 687.3 UPLC1 139

2.05 705.28 UPLC1 140

2.13 755.3 UPLC1 141

2.12 739.27 UPLC1 142

2.07 723.29 UPLC1 143

2.07 723.28 UPLC1 144

2.15 773.29 UPLC1 145

2.04 661.33 UPLC1 146

2.08 657.35 UPLC1 147

2.09 677.01 UPLC1 148

2.26 688.34 UPLC1 149

2.09 657.35 UPLC1 150

2.09 675.36 UPLC1 151

2.12 695.32 UPLC1 152

2.08 722.3 UPLC1 153

2.16 727.35 UPLC1 154

2.03 673.36 UPLC1 155

2.03 643.33 UPLC1 156

2.04 661.34 UPLC1 157

2.12 711.43 UPLC1 158

2.11 695.31 UPLC1 159

2.06 679.33 UPLC1 160

2.06 679.33 UPLC1 161

2.14 729.35 UPLC1 162

2.02 732.29 UPLC1 163

2.16 773.29 UPLC1 164

1.15 661 UPLC2 Short 165

1.14 679.06 UPLC2 Short 166

1.10 709 UPLC2 Short 167

1.10 689 UPLC2 Short 168

1.11 707 UPLC2 Short 169

1.24 754 UPLC2 Short 170

1.14 761 UPLC2 Short 171

1.12 743 UPLC2 Short 172

1.12 727 UPLC2 Short 173

1.09 645 UPLC2 Short 174

1.10 663 UPLC2 Short 175

1.14 717 UPLC2 Short 176

1.06 661 UPLC2 Short 177

1.08 667 UPLC2 Short 178

1.30 755 UPLC2 Short 179

1.17 727 UPLC2 Short 180

1.17 729.05 UPLC2 Short 181

1.30 711.1 UPLC2 Short 182

73-77 183

1.00 690 ZCQ13LC-MS Method: ZCQ13

ZQ Mass Spectrometer from Waters (Single quadrupole mass spectrometer)

Instrument Parameter:

-   -   Ionization method: Electrospray    -   Polarity: positive and negative ions    -   Capillary: 3.00 kV    -   Cone: 30 V    -   Extractor: 2.00 V    -   Source Temperature: 150° C.,    -   Desolvation Temperature: 350 C    -   Cone Gas Flow: 50 L/Hr    -   Desolvation Gas Flow: 400 L/Hr    -   Mass range: 100 to 900 Da

Acquity UPLC from Waters:

-   -   Binary pump, heated column compartment and diode-array detector.    -   Solvent degasser, binary pump, heated column compartment and        diode-array detector.    -   Column: Waters UPLC HSS T3, 1.8 μm, 30×2.1 mm,    -   Temp: 60° C.    -   DAD Wavelength range (nm): 210 to 500    -   Solvent Gradient:        -   A=H2O+5% MeOH+0.05% HCOOH        -   B=Acetonitrile+0.05% HCOOH

Time A % B % Flow (ml/min) 0.00 90 10 0.85 1.20 0 100.0 0.85 1.50 0100.0 0.85LC-MS Method: SQD13

SQD Mass Spectrometer from Waters (Single quadrupole mass spectrometer)

Instrument Parameter:

-   -   Ionization method: Electrospray    -   Polarity: positive and negative ions    -   Capillary: 3.00 kV    -   Cone: 30V    -   Extractor: 2.00 V    -   Source Temperature: 150° C.,    -   Desolvation Temperature: 350° C.    -   Cone Gas Flow: 50 L/Hr    -   Desolvation Gas Flow: 650 L/Hr    -   Mass range: 100 to 900 Da

Acquity UPLC from Waters:

-   -   Binary pump, heated column compartment and diode-array detector.    -   Solvent degasser, binary pump, heated column compartment and        diode-array detector.    -   Column: Waters UPLC HSS T3, 1.8 μm, 30×2.1 mm,    -   Temp: 60° C.    -   DAD Wavelength range (nm): 210 to 500    -   Solvent Gradient:        -   A=H2O+5% MeOH+0.05% HCOOH        -   B=Acetonitrile+0.05% HCOOH

Time A % B % Flow (ml/min) 0.00 90 10 0.85 1.20 0 100.0 0.85 1.50 0100.0 0.85LC-MS Method: UPLC1

ACQUITY SQD Mass Spectrometer from Waters (Single quadrupole massspectrometer)

Ionisation method: Electrospray

Polarity: positive ions

Capillary (kV) 3.00, Cone (V) 20.00, Extractor (V) 3.00, SourceTemperature (° C.) 150, Desolvation Temperature (° C.) 400, Cone GasFlow (L/Hr) 60, Desolvation Gas Flow (L/Hr) 700

Mass range: 100 to 800 Da

DAD Wavelength range (nm): 210 to 400

Method Waters ACQUITY UPLC with the following HPLC gradient conditions

(Solvent A: Water/Methanol 9:1, 0.1% formic acid and Solvent B:Acetonitrile, 0.1% formic acid)

Time (minutes) A (%) B (%) Flow rate (ml/min) 0 100 0 0.75 2.5 0 1000.75 2.8 0 100 0.75 3.0 100 0 0.75

Type of column: Waters ACQUITY UPLC HSS T3; Column length: 30 mm;Internal diameter of column: 2.1 mm; Particle Size: 1.8 micron;Temperature: 60° C.

LC-MS Method: UPLC2

ZQ2000 Mass Spectrometer from Waters (Single quadrupole massspectrometer)

Ionisation method: Electrospray

Polarity: positive ions

Capillary (kV) 3.5, Cone (V) 60.00, Extractor (V) 3.00, SourceTemperature (° C.) 150, Desolvation Temperature (° C.) 350, Cone GasFlow (L/Hr) 50, Desolvation Gas Flow (L/Hr) 800

Mass range: 140 to 800 Da

DAD Wavelength range (nm): 210 to 400

Method Waters ACQUITY UPLC with the following HPLC gradient conditions

(Solvent A: Water/Methanol 9:1, 0.1% formic acid and Solvent B:Acetonitrile, 0.1% formic acid)

Time (minutes) A (%) B (%) Flow rate (ml/min) 0 100 0 0.75 2.5 0 1000.75 2.8 0 100 0.75 3.0 100 0 0.75

Type of column: Waters ACQUITY UPLC HSS T3; Column length: 30 mm;Internal diameter of column: 2.1 mm; Particle Size: 1.8 micron;Temperature: 60° C.

LC-MS Method: UPLC2 Short

ZQ2000 Mass Spectrometer from Waters (Single quadrupole massspectrometer)

Ionisation method: Electrospray

Polarity: positive ions

Capillary (kV) 3.5, Cone (V) 60.00, Extractor (V) 3.00, SourceTemperature (° C.) 150, Desolvation Temperature (° C.) 350, Cone GasFlow (L/Hr) 50, Desolvation Gas Flow (L/Hr) 800

Mass range: 140 to 800 Da

DAD Wavelength range (nm): 210 to 400

Method Waters ACQUITY UPLC with the following HPLC gradient conditions

(Solvent A: Water/Methanol 9:1, 0.1% formic acid and Solvent B:Acetonitrile, 0.1% formic acid)

Time (minutes) A (%) B (%) Flow rate (ml/min) 0 80 20 1 0.1 75 25 1 0.270 30 0.75 1.2 0 100 0.75 1.4 0 100 0.75 1.45 80 20 0.75

Type of column: Waters ACQUITY UPLC HSS T3; Column length: 30 mm;Internal diameter of column: 2.1 mm; Particle Size: 1.8 micron;Temperature: 60° C.

BIOLOGICAL EXAMPLES

These Examples illustrate the insecticidal and acaricidal properties ofthe compounds of formula (I). The tests were performed as follows:

Diabrotica balteata (Corn Root Worm):

A 24-well microtiter plate (MTP) with artificial diet was treated withtest solutions at an application rate of 200 ppm (concentration in well18 ppm) by pipetting. After drying, the MTP's were infested with L2larvae (6-10 per well). After an incubation period of 5 days, sampleswere checked for larval mortality.

The following compound gave at least 80% control of Diabrotica balteata:1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20,21, 22, 23, 24, 25, 26, 27, 28, 31, 32, 33, 35, 36, 37, 38, 39, 40, 41,42, 43, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60,61, 62, 63, 64, 66, 68, 69, 70, 71, 74, 76, 77, 78, 79, 80, 81, 82, 83,84, 86, 87, 89, 90, 91, 92, 93, 94, 95, 99, 100, 101, 102, 103, 104,105, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120,121, 122, 123, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 135,136, 138, 139, 140, 141, 142, 143, 145, 146, 147, 148, 149, 150, 151,152, 153, 154, 155, 156, 157, 158, 159, 160, 162, 163, 183.

Myzus persicae (Green Peach Aphid):

Sunflower leaf discs were placed on agar in a 24-well microtiter plateand sprayed with test solutions at an application rate of 200 ppm. Afterdrying, the leaf discs were infested with an aphid population of mixedages. After an incubation period of 6 DAT, samples were checked formortality.

The following compounds gave at least 80% control of Myzus persicae: 1,2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21,22, 23, 24, 25, 26, 27, 28, 31, 32, 35, 36, 37, 38, 39, 40, 41, 43, 45,47, 48, 49, 50, 51, 52, 53, 54, 56, 57, 59, 60, 61, 63, 64, 66, 68, 69,70, 71, 73, 76, 78, 79, 81, 82, 83, 84, 86, 89, 92, 93, 94, 95, 96, 97,99, 100, 101, 102, 103, 105, 108, 109, 111, 112, 119, 120, 122, 123,125, 127, 128, 131, 132, 135, 138, 139, 140, 141, 142, 143, 147, 149,155, 156, 158, 159, 162.

Myzus persicae (Green Peach Aphid):

Test compounds were applied by pipette into 24 well plates and mixedwith Sucrose solution. Application rate: 12.5 ppm. The plates wereclosed with a stretched Parafilm. A plastic stencil with 24 holes isplaced onto the plate and infested pea seedlings were placed directly onthe Parafilm. The infested plate is closed with a gel blotting paper andanother plastic stencil and then turned upside down. 5 days afterinfestation the samples were checked on mortality.

The following compounds gave at least 80% control of Myzus persicae: 1,2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21,22, 23, 24, 25, 26, 27, 28, 31, 32, 33, 36, 38, 39, 40, 41, 44, 45, 47,49, 50, 51, 53, 54, 56, 57, 59, 60, 61, 62, 64, 66, 68, 70, 74, 76, 78,81, 83, 84, 86, 89, 93, 99, 100, 101, 102, 103, 104, 105, 108, 109, 110,111, 113, 114, 115, 116, 117, 119, 120, 122, 123, 125, 126, 127, 128,135, 138, 139, 141, 152, 155, 156, 158, 159, 160, 162, 183.

Plutella xylostella (Diamond Back Moth):

24-well microtiter plate (MTP) with artificial diet was treated withtest solutions at an application rate of 200 ppm (concentration in well18 ppm) by pipetting. After drying, the MTP's were infested with L2larvae (7-12 per well). After an incubation period of 6 days, sampleswere checked for larval mortality.

The following compound gave at least 80% control of Plutella xylostella:1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20,21, 22, 23, 24, 25, 26, 27, 28, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40,41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58,59, 60, 61, 62, 63, 64, 66, 68, 69, 70, 71, 72, 74, 75, 76, 77, 78, 79,80, 81, 82, 83, 84, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 99,100, 101, 102, 103, 104, 105, 108, 109, 110, 111, 112, 113, 114, 115,117, 118, 119, 120, 121, 122, 123, 125, 126, 127, 128, 129, 130, 131,132, 133, 134, 135, 138, 139, 140, 141, 142, 143, 144, 145, 146, 147,149, 150, 151, 152, 154, 155, 156, 157, 158, 159, 160, 162, 163.

Spodoptera littoralis (Egyptian Cotton Leafworm):

Cotton leaf discs were placed on agar in a 24-well microtiter plate andsprayed with test solutions at an application rate of 200 ppm. Afterdrying, the leaf discs were infested with 5 L1 larvae. The samples werechecked for mortality 3 days after treatment (DAT).

The following compound gave at least 80% control of Spodopteralittoralis: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17,18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 31, 32, 33, 34, 35, 36, 37,38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55,56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 68, 69, 70, 71, 72, 73, 74,75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92,93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 108, 109, 110,111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 125,126, 127, 128, 129, 130, 131, 132, 133, 134, 135, 138, 139, 140, 141,142, 143, 144, 145, 146, 147, 149, 150, 151, 152, 154, 155, 156, 157,158, 159, 160, 162.

Tetranychus urticae (Two-Spotted Spider Mite):

Bean leaf discs on agar in 24-well microtiter plates were sprayed withtest solutions at an application rate of 200 ppm. After drying, the leafdiscs are infested with mite populations of mixed ages. 8 days later,discs are checked for egg mortality, larval mortality, and adultmortality.

The following compounds gave at least 80% control of Tetranychusurticae: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18,19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 31, 32, 35, 36, 37, 38, 39, 40,43, 46, 47, 48, 49, 50, 51, 53, 54, 57, 60, 61, 62, 64, 66, 68, 70, 71,74, 76, 77, 78, 79, 81, 83, 84, 86, 87, 89, 92, 93, 94, 95, 97, 99, 100,101, 102, 103, 108, 109, 112, 119, 120, 122, 127, 128, 129, 133, 135,139, 141, 152, 154, 156, 158, 162.

Thrips tabaci (Onion Thrips):

Sunflower leaf discs were placed on agar in a 24-well microtiter plateand sprayed with test solutions at an application rate of 200 ppm. Afterdrying, the leaf discs were infested with an aphid population of mixedages. After an incubation period of 7 days, samples were checked formortality.

The following compounds gave at least 80% control of Thrips tabaci: 1,2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21,22, 23, 24, 25, 26, 27, 28, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41,42, 43, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60,61, 63, 64, 66, 68, 69, 70, 71, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83,84, 86, 87, 88, 89, 90, 92, 93, 94, 95, 97, 99, 100, 101, 102, 103, 104,105, 108, 109, 110, 111, 112, 114, 115, 116, 117, 119, 120, 121, 122,123, 125, 126, 127, 128, 129, 131, 132, 133, 134, 135, 138, 139, 140,141, 142, 143, 144, 145, 147, 148, 149, 150, 151, 152, 153, 154, 155,156, 157, 158, 159, 160, 162, 163.

The invention claimed is:
 1. A compound of formula (I)

wherein Y is chlorine, bromine, iodine, C₁-C₄ alkyl, C₁-C₄ haloalkyl orC₁-C₄ haloalkoxy, X₁ is methoxy and X₂ is hydrogen, or X₂ is cyano andX₁ is hydrogen, R is hydrogen or C₁-C₄ alkyl Q is a group selected fromQ1, Q2, Q3, Q4 and Q5, where Q1 is a group of formula (IIa)

Where the substituents W1 are independently selected from, hydrogen,halogen, cyano, nitro, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy orC₁-C₄ haloalkoxy, n1 is 0, 1 or 2 Q2 is a group of formula (IIb)

Where W₂ is selected from, hydrogen, halogen, cyano, C₁-C₄ alkyl, C₁-C₄haloalkyl, C₁-C₄ alkoxy or C₁-C₄ haloalkoxy, Q3 is a group of formula(IIc)

Where W₃ is selected from, hydrogen, halogen, cyano, C₁-C₄ alkyl, C₁-C₄haloalkyl, C₁-C₄ alkoxy or C₁-C₄ haloalkoxy, Q4 is a group of formula(IId)

Where W₄ is selected, hydrogen, halogen, cyano, C₁-C₄ alkyl, C₁-C₄haloalkyl, C₁-C₄ alkoxy or C₁-C₄ haloalkoxy, Q5 is a group of formula(IIe)

Where W₅ is selected from hydrogen, hydrogen, halogen, cyano, C₁-C₄alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy or C₁-C₄ haloalkoxy, or anagrochemically acceptable salt thereof.
 2. A compound of formula (I)according to claim 1 wherein Q is a group selected from Q1, Q2, Q3, Q4and Q5, where Q1 is a group of formula (IIa)

where the substituents W₁ is cyano, and n1 is 1 Q2 is a group of formula(IIb)

where W₂ is hydrogen, Q3 is a group of formula (IIc)

where W₃ is hydrogen, Q4 is a group of formula (IId)

where W₄ is hydrogen Q5 is a group of formula (IIe)

where W₅ is hydrogen.
 3. A compound of formula (I) according to claim 1wherein R is hydrogen, methyl or ethyl.
 4. A compound of formula (I)according to claim 1 wherein X₁ is methoxy and X₂ is hydrogen.
 5. Acompound of formula (I) according to claim 4 wherein X₂ is cyano and X₁is hydrogen.
 6. A compound of formula (III)

where Y is chlorine, bromine, iodine, C₁-C₄ alkyl, C₁-C₄ haloalkyl orC₁-C₄ haloalkoxy.
 7. A method of controlling insects, acarines,nematodes or molluscs which comprises applying to a pest, to a locus ofa pest, or to a plant susceptible to attack by a pest an insecticidally,acaricidally, nematicidally or molluscicidally effective amount of acompound of formula (I) as defined in claim
 1. 8. An insecticidal,acaricidal, nematicidal or molluscicidal composition comprising aninsecticidally, acaricidally, nematicidally or molluscicidally effectiveamount of a compound of formula (I) as defined in claim 1 together withan agrochemically acceptable diluent or carrier.
 9. A compositionaccording to claim 8 which further comprises one or more additionalinsecticidal, acaricidal, nematicidal or molluscicidal compounds.
 10. Amethod of protecting useful plants from insects, acarines, nematodes ormolluscs, comprising applying to said plants, to the locus thereof, orto plant propagation material thereof, an insecticidally, acaricidally,nematicidally or molluscicidally effective amount of a compound offormula I in claim 1.